# Supplementary Information (SI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a
_database_code_depnum_ccdc_archive 'CCDC 2504593'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H17 Cl2 N Ru'
_chemical_formula_weight         347.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.745(2)
_cell_length_b                   10.958(3)
_cell_length_c                   12.730(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.973(5)
_cell_angle_gamma                90
_cell_volume                     1342.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4471
_cell_measurement_theta_min      2.4655
_cell_measurement_theta_max      26.3945

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    1.538
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3829
_exptl_absorpt_correction_T_max  0.5624
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1264 (selected reflections only, before parameter refinement)
 R(int) =  0.0715 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11631
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.116
_diffrn_reflns_theta_max         25.090
_diffrn_reflns_theta_full        25.090
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2353
_reflns_number_gt                1964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0730P)²+12.2309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     197
_refine_ls_number_restraints     202
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1681
_refine_ls_wR_factor_gt          0.1599
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.32553(7) 0.22656(6) 0.56278(5) 0.0158(3) Uani 1 1 d . . . . .
Cl1 Cl 0.1557(2) 0.2746(2) 0.67599(17) 0.0259(5) Uani 1 1 d . . . . .
Cl2 Cl 0.3737(3) 0.0407(2) 0.66324(19) 0.0339(6) Uani 1 1 d . . . . .
C1 C 0.1690(11) 0.1426(8) 0.4735(7) 0.028(2) Uani 1 1 d D U . . .
N1 N 0.0608(17) 0.1165(17) 0.4180(14) 0.024(2) Uani 0.501(16) 1 d D U P A 1
C2 C -0.0624(18) 0.0790(18) 0.3448(14) 0.023(3) Uani 0.501(16) 1 d D U P A 1
H2A H -0.056161 0.109457 0.273286 0.035 Uiso 0.501(16) 1 calc R U P A 1
H2B H -0.145502 0.112539 0.368606 0.035 Uiso 0.501(16) 1 calc R U P A 1
H2C H -0.068198 -0.010331 0.343183 0.035 Uiso 0.501(16) 1 calc R U P A 1
N2 N 0.101(2) 0.0799(16) 0.4173(14) 0.024(2) Uani 0.499(16) 1 d D U P A 2
C200 C 0.0006(19) 0.0253(17) 0.3383(14) 0.023(3) Uani 0.499(16) 1 d D U P A 2
H20A H -0.092907 0.044814 0.352584 0.035 Uiso 0.499(16) 1 calc R U P A 2
H20B H 0.013456 -0.063385 0.339567 0.035 Uiso 0.499(16) 1 calc R U P A 2
H20C H 0.011967 0.056909 0.268116 0.035 Uiso 0.499(16) 1 calc R U P A 2
C11 C 0.3264(11) 0.4022(11) 0.4799(10) 0.044(2) Uani 1 1 d D U . . .
C12 C 0.3981(11) 0.4147(10) 0.5816(10) 0.039(2) Uani 1 1 d . U . . .
H12 H 0.355203 0.467454 0.631791 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5101(10) 0.3411(8) 0.6255(8) 0.0253(19) Uani 1 1 d . U . . .
H13 H 0.543750 0.343869 0.703780 0.030 Uiso 1 1 calc R U . . .
C14 C 0.5546(9) 0.2459(7) 0.5640(7) 0.0216(17) Uani 1 1 d D U . . .
C15 C 0.4832(10) 0.2290(11) 0.4589(8) 0.034(2) Uani 1 1 d . U . . .
H15 H 0.500570 0.153954 0.418256 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3714(11) 0.3079(12) 0.4190(9) 0.043(2) Uani 1 1 d . U . . .
H16 H 0.311708 0.285558 0.350474 0.052 Uiso 1 1 calc R U . . .
C17 C 0.2091(17) 0.4570(17) 0.3991(14) 0.022(4) Uani 0.489(12) 1 d D U P B 1
H17A H 0.165418 0.392424 0.352046 0.033 Uiso 0.489(12) 1 calc R U P B 1
H17B H 0.247440 0.519314 0.356647 0.033 Uiso 0.489(12) 1 calc R U P B 1
H17C H 0.139504 0.494249 0.436912 0.033 Uiso 0.489(12) 1 calc R U P B 1
C18 C 0.6666(19) 0.168(2) 0.6272(13) 0.023(4) Uani 0.489(12) 1 d D U P B 1
H18 H 0.637707 0.081267 0.613951 0.027 Uiso 0.489(12) 1 calc R U P B 1
C19 C 0.698(2) 0.1837(19) 0.7472(13) 0.031(5) Uani 0.489(12) 1 d D U P B 1
H19A H 0.771534 0.126447 0.776548 0.047 Uiso 0.489(12) 1 calc R U P B 1
H19B H 0.614231 0.167344 0.778203 0.047 Uiso 0.489(12) 1 calc R U P B 1
H19C H 0.729495 0.267477 0.764061 0.047 Uiso 0.489(12) 1 calc R U P B 1
C20 C 0.7953(17) 0.1873(17) 0.5741(16) 0.022(4) Uani 0.489(12) 1 d D U P B 1
H20D H 0.773274 0.166238 0.498506 0.033 Uiso 0.489(12) 1 calc R U P B 1
H20E H 0.870810 0.135018 0.608346 0.033 Uiso 0.489(12) 1 calc R U P B 1
H20F H 0.824170 0.272955 0.581289 0.033 Uiso 0.489(12) 1 calc R U P B 1
C27 C 0.675(2) 0.1579(19) 0.5875(18) 0.023(4) Uani 0.511(12) 1 d D U P B 2
H27A H 0.676380 0.121932 0.658115 0.034 Uiso 0.511(12) 1 calc R U P B 2
H27B H 0.762668 0.201775 0.585814 0.034 Uiso 0.511(12) 1 calc R U P B 2
H27C H 0.665342 0.093039 0.533854 0.034 Uiso 0.511(12) 1 calc R U P B 2
C28 C 0.2073(15) 0.4972(14) 0.4678(14) 0.025(3) Uani 0.511(12) 1 d D U P B 2
H28 H 0.225611 0.552688 0.409198 0.030 Uiso 0.511(12) 1 calc R U P B 2
C29 C 0.0740(17) 0.4274(17) 0.4230(15) 0.027(4) Uani 0.511(12) 1 d D U P B 2
H29A H 0.087858 0.384158 0.358073 0.041 Uiso 0.511(12) 1 calc R U P B 2
H29B H -0.003138 0.485190 0.406422 0.041 Uiso 0.511(12) 1 calc R U P B 2
H29C H 0.052236 0.368422 0.475862 0.041 Uiso 0.511(12) 1 calc R U P B 2
C30 C 0.1741(19) 0.5821(16) 0.5569(14) 0.027(4) Uani 0.511(12) 1 d D U P B 2
H30A H 0.096986 0.636141 0.528740 0.041 Uiso 0.511(12) 1 calc R U P B 2
H30B H 0.256256 0.631153 0.583570 0.041 Uiso 0.511(12) 1 calc R U P B 2
H30C H 0.148048 0.532970 0.614997 0.041 Uiso 0.511(12) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C1 1.981(10) . ?
Ru1 C16 2.145(10) . ?
Ru1 C15 2.177(10) . ?
Ru1 C12 2.181(11) . ?
Ru1 C11 2.196(10) . ?
Ru1 C13 2.236(9) . ?
Ru1 C14 2.240(9) . ?
Ru1 Cl2 2.411(2) . ?
Ru1 Cl1 2.416(2) . ?
C1 N2 1.130(15) . ?
C1 N1 1.209(15) . ?
N1 C2 1.459(17) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 C200 1.420(17) . ?
C200 H20A 0.9800 . ?
C200 H20B 0.9800 . ?
C200 H20C 0.9800 . ?
C11 C12 1.380(17) . ?
C11 C16 1.403(18) . ?
C11 C17 1.536(15) . ?
C11 C28 1.549(15) . ?
C12 C13 1.401(15) . ?
C12 H12 1.0000 . ?
C13 C14 1.413(13) . ?
C13 H13 1.0000 . ?
C14 C15 1.420(13) . ?
C14 C18 1.514(16) . ?
C14 C27 1.515(16) . ?
C15 C16 1.421(16) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.519(17) . ?
C18 C20 1.529(17) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20D 0.9800 . ?
C20 H20E 0.9800 . ?
C20 H20F 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.538(16) . ?
C28 C30 1.539(16) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ru1 C16 87.0(4) . . ?
C1 Ru1 C15 102.1(4) . . ?
C16 Ru1 C15 38.4(4) . . ?
C1 Ru1 C12 135.2(4) . . ?
C16 Ru1 C12 66.1(5) . . ?
C15 Ru1 C12 78.9(4) . . ?
C1 Ru1 C11 101.0(4) . . ?
C16 Ru1 C11 37.7(5) . . ?
C15 Ru1 C11 69.0(4) . . ?
C12 Ru1 C11 36.8(5) . . ?
C1 Ru1 C13 165.9(4) . . ?
C16 Ru1 C13 79.0(4) . . ?
C15 Ru1 C13 66.8(4) . . ?
C12 Ru1 C13 37.0(4) . . ?
C11 Ru1 C13 67.4(4) . . ?
C1 Ru1 C14 136.5(4) . . ?
C16 Ru1 C14 68.1(4) . . ?
C15 Ru1 C14 37.5(4) . . ?
C12 Ru1 C14 66.7(3) . . ?
C11 Ru1 C14 80.9(3) . . ?
C13 Ru1 C14 36.8(3) . . ?
C1 Ru1 Cl2 88.9(3) . . ?
C16 Ru1 Cl2 139.0(4) . . ?
C15 Ru1 Cl2 103.6(3) . . ?
C12 Ru1 Cl2 135.0(3) . . ?
C11 Ru1 Cl2 168.5(3) . . ?
C13 Ru1 Cl2 101.9(3) . . ?
C14 Ru1 Cl2 88.0(2) . . ?
C1 Ru1 Cl1 84.6(3) . . ?
C16 Ru1 Cl1 132.2(4) . . ?
C15 Ru1 Cl1 166.7(3) . . ?
C12 Ru1 Cl1 88.2(3) . . ?
C11 Ru1 Cl1 98.6(3) . . ?
C13 Ru1 Cl1 104.6(2) . . ?
C14 Ru1 Cl1 138.6(2) . . ?
Cl2 Ru1 Cl1 87.85(9) . . ?
N2 C1 Ru1 165.8(14) . . ?
N1 C1 Ru1 165.7(12) . . ?
C1 N1 C2 174.8(19) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N2 C200 167(2) . . ?
N2 C200 H20A 109.5 . . ?
N2 C200 H20B 109.5 . . ?
H20A C200 H20B 109.5 . . ?
N2 C200 H20C 109.5 . . ?
H20A C200 H20C 109.5 . . ?
H20B C200 H20C 109.5 . . ?
C12 C11 C16 115.9(10) . . ?
C12 C11 C17 143.6(13) . . ?
C16 C11 C17 100.5(12) . . ?
C12 C11 C28 106.7(12) . . ?
C16 C11 C28 137.3(12) . . ?
C12 C11 Ru1 71.0(6) . . ?
C16 C11 Ru1 69.2(6) . . ?
C17 C11 Ru1 127.3(9) . . ?
C28 C11 Ru1 125.3(9) . . ?
C11 C12 C13 124.5(11) . . ?
C11 C12 Ru1 72.2(7) . . ?
C13 C12 Ru1 73.7(6) . . ?
C11 C12 H12 117.1 . . ?
C13 C12 H12 117.1 . . ?
Ru1 C12 H12 117.1 . . ?
C12 C13 C14 119.5(9) . . ?
C12 C13 Ru1 69.4(6) . . ?
C14 C13 Ru1 71.8(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
Ru1 C13 H13 119.6 . . ?
C13 C14 C15 118.1(9) . . ?
C13 C14 C18 112.3(10) . . ?
C15 C14 C18 129.4(11) . . ?
C13 C14 C27 131.0(11) . . ?
C15 C14 C27 110.8(11) . . ?
C13 C14 Ru1 71.4(5) . . ?
C15 C14 Ru1 68.9(5) . . ?
C18 C14 Ru1 125.8(10) . . ?
C27 C14 Ru1 133.1(11) . . ?
C14 C15 C16 119.6(10) . . ?
C14 C15 Ru1 73.6(5) . . ?
C16 C15 Ru1 69.6(6) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
Ru1 C15 H15 119.8 . . ?
C11 C16 C15 122.6(10) . . ?
C11 C16 Ru1 73.1(6) . . ?
C15 C16 Ru1 72.1(6) . . ?
C11 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
Ru1 C16 H16 118.2 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 C19 119.2(15) . . ?
C14 C18 C20 105.1(13) . . ?
C19 C18 C20 112.2(17) . . ?
C14 C18 H18 106.5 . . ?
C19 C18 H18 106.5 . . ?
C20 C18 H18 106.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20D 109.5 . . ?
C18 C20 H20E 109.5 . . ?
H20D C20 H20E 109.5 . . ?
C18 C20 H20F 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
C14 C27 H27A 109.5 . . ?
C14 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C14 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C30 108.2(13) . . ?
C29 C28 C11 106.2(12) . . ?
C30 C28 C11 125.0(14) . . ?
C29 C28 H28 105.3 . . ?
C30 C28 H28 105.3 . . ?
C11 C28 H28 105.3 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_refine_diff_density_max         2.127
_refine_diff_density_min         -1.416
_refine_diff_density_rms         0.213

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1g
_database_code_depnum_ccdc_archive 'CCDC 2504596'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 Cl5 N O Ru'
_chemical_formula_weight         558.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3192(14)
_cell_length_b                   12.9409(18)
_cell_length_c                   18.335(2)
_cell_angle_alpha                71.028(4)
_cell_angle_beta                 89.935(4)
_cell_angle_gamma                78.471(3)
_cell_volume                     2263.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.264
_cell_measurement_theta_max      27.2415

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.293
_shelx_estimated_absorpt_T_min   0.747
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2913
_exptl_absorpt_correction_T_max  0.4302
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1588 (selected reflections only, before parameter refinement)
 R(int) =  0.0812 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24777
_diffrn_reflns_av_unetI/netI     0.0879
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.702
_diffrn_reflns_theta_max         26.024
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             8611
_reflns_number_gt                7356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+16.7364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8611
_refine_ls_number_parameters     496
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1620
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.206
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.57670(7) 0.99022(5) 0.15145(4) 0.01131(17) Uani 1 1 d . . . . .
Cl1 Cl 0.3575(2) 0.95359(17) 0.15495(12) 0.0171(4) Uani 1 1 d . . . . .
Cl2 Cl 0.6525(2) 0.82137(18) 0.12165(12) 0.0188(5) Uani 1 1 d . . . . .
C1 C 0.7338(10) 1.0613(7) 0.0837(5) 0.0200(18) Uani 1 1 d . U . . .
C2 C 0.7336(10) 1.0779(7) 0.1561(5) 0.0180(17) Uani 1 1 d . U . . .
H2 H 0.811540 1.038874 0.194178 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6193(8) 1.1294(7) 0.1803(5) 0.0144(16) Uani 1 1 d . U . . .
H3 H 0.618336 1.125325 0.235701 0.017 Uiso 1 1 calc R U . . .
C4 C 0.4993(9) 1.1671(7) 0.1358(5) 0.0188(17) Uani 1 1 d . U . . .
C5 C 0.5017(10) 1.1543(7) 0.0605(5) 0.0204(19) Uani 1 1 d . U . . .
H5 H 0.414898 1.165711 0.031708 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6127(10) 1.1023(7) 0.0360(5) 0.0202(18) Uani 1 1 d . U . . .
H6 H 0.604428 1.078523 -0.010219 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8568(10) 1.0040(8) 0.0565(6) 0.025(2) Uani 1 1 d . U . . .
H7A H 0.896939 1.060274 0.019488 0.037 Uiso 1 1 calc R U . . .
H7B H 0.833192 0.953371 0.031426 0.037 Uiso 1 1 calc R U . . .
H7C H 0.920224 0.961224 0.100863 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3734(10) 1.2218(8) 0.1608(6) 0.0248(19) Uani 1 1 d . U . . .
H8 H 0.298707 1.197698 0.140557 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3680(12) 1.1889(9) 0.2469(6) 0.034(2) Uani 1 1 d . U . . .
H9A H 0.393439 1.107337 0.269869 0.051 Uiso 1 1 calc R U . . .
H9B H 0.277609 1.214716 0.259550 0.051 Uiso 1 1 calc R U . . .
H9C H 0.429282 1.223083 0.267481 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3525(15) 1.3477(10) 0.1241(7) 0.053(3) Uani 1 1 d . U . . .
H10A H 0.426200 1.373545 0.141253 0.079 Uiso 1 1 calc R U . . .
H10B H 0.269082 1.383351 0.139509 0.079 Uiso 1 1 calc R U . . .
H10C H 0.348825 1.367491 0.067651 0.079 Uiso 1 1 calc R U . . .
N1 N 0.6133(8) 0.8306(6) 0.3219(4) 0.0168(16) Uani 1 1 d . . . . .
C11 C 0.6016(9) 0.8917(7) 0.2590(5) 0.0151(18) Uani 1 1 d . . . . .
C12 C 0.6344(9) 0.7582(7) 0.3987(5) 0.0155(17) Uani 1 1 d . U . . .
C13 C 0.6156(9) 0.6508(8) 0.4168(5) 0.0204(18) Uani 1 1 d . U . . .
H13 H 0.582180 0.626996 0.378135 0.025 Uiso 1 1 calc R U . . .
C14 C 0.6453(9) 0.5779(8) 0.4910(5) 0.0178(17) Uani 1 1 d . U . . .
H14 H 0.632739 0.503491 0.503743 0.021 Uiso 1 1 calc R U . . .
C15 C 0.6941(9) 0.6139(7) 0.5477(5) 0.0155(17) Uani 1 1 d . U . . .
C16 C 0.7125(9) 0.7216(7) 0.5298(5) 0.0157(17) Uani 1 1 d . U . . .
H16 H 0.745608 0.745427 0.568559 0.019 Uiso 1 1 calc R U . . .
C17 C 0.6825(9) 0.7951(7) 0.4547(5) 0.0178(18) Uani 1 1 d . U . . .
H17 H 0.694549 0.869745 0.441676 0.021 Uiso 1 1 calc R U . . .
O1 O 0.7219(7) 0.5349(5) 0.6196(3) 0.0204(14) Uani 1 1 d . . . . .
C18 C 0.7791(12) 0.5657(8) 0.6774(5) 0.029(2) Uani 1 1 d . . . . .
H18A H 0.862867 0.587520 0.660817 0.044 Uiso 1 1 calc R U . . .
H18B H 0.796018 0.502063 0.725677 0.044 Uiso 1 1 calc R U . . .
H18C H 0.718191 0.628685 0.685773 0.044 Uiso 1 1 calc R U . . .
Ru2 Ru 0.92913(7) 1.00701(5) 0.64726(4) 0.01107(17) Uani 1 1 d . . . . .
Cl3 Cl 1.1679(2) 0.96127(17) 0.65111(12) 0.0154(4) Uani 1 1 d . . . . .
Cl4 Cl 0.9343(2) 0.83163(17) 0.62746(12) 0.0166(4) Uani 1 1 d . . . . .
C21 C 0.7378(10) 1.0793(7) 0.5768(5) 0.0196(18) Uani 1 1 d . U . . .
C22 C 0.8417(9) 1.1115(7) 0.5282(5) 0.0195(18) Uani 1 1 d . U . . .
H22 H 0.860867 1.082221 0.484243 0.023 Uiso 1 1 calc R U . . .
C23 C 0.9309(9) 1.1631(7) 0.5512(5) 0.0150(17) Uani 1 1 d . U . . .
H23 H 1.013610 1.169709 0.523138 0.018 Uiso 1 1 calc R U . . .
C24 C 0.9233(9) 1.1852(8) 0.6230(5) 0.0192(18) Uani 1 1 d . U . . .
C25 C 0.8208(9) 1.1556(7) 0.6680(5) 0.0162(17) Uani 1 1 d . U . . .
H25 H 0.822227 1.158282 0.721898 0.019 Uiso 1 1 calc R U . . .
C26 C 0.7281(9) 1.1036(7) 0.6454(5) 0.0160(17) Uani 1 1 d . U . . .
H26 H 0.666496 1.069933 0.683842 0.019 Uiso 1 1 calc R U . . .
C27 C 0.6423(11) 1.0210(8) 0.5528(6) 0.029(2) Uani 1 1 d . U . . .
H27A H 0.599313 0.981719 0.598074 0.044 Uiso 1 1 calc R U . . .
H27B H 0.690314 0.967104 0.529881 0.044 Uiso 1 1 calc R U . . .
H27C H 0.574924 1.076195 0.514618 0.044 Uiso 1 1 calc R U . . .
C28 C 1.0277(10) 1.2404(8) 0.6440(6) 0.0245(19) Uani 1 1 d . U . . .
H28 H 1.115988 1.198903 0.635691 0.029 Uiso 1 1 calc R U . . .
C29 C 1.0089(11) 1.3600(8) 0.5889(7) 0.035(3) Uani 1 1 d . U . . .
H29A H 1.015285 1.359532 0.535648 0.053 Uiso 1 1 calc R U . . .
H29B H 1.077852 1.394883 0.601462 0.053 Uiso 1 1 calc R U . . .
H29C H 0.921468 1.402439 0.594039 0.053 Uiso 1 1 calc R U . . .
C30 C 1.0302(12) 1.2344(10) 0.7272(7) 0.041(3) Uani 1 1 d . U . . .
H30A H 0.948678 1.281149 0.736148 0.061 Uiso 1 1 calc R U . . .
H30B H 1.106982 1.261459 0.739330 0.061 Uiso 1 1 calc R U . . .
H30C H 1.036631 1.156842 0.760527 0.061 Uiso 1 1 calc R U . . .
N2 N 0.9644(8) 0.8578(6) 0.8212(4) 0.0169(16) Uani 1 1 d . . . . .
C31 C 0.9480(10) 0.9149(7) 0.7575(5) 0.0197(19) Uani 1 1 d . . . . .
C32 C 0.9855(10) 0.7793(7) 0.8951(5) 0.0175(17) Uani 1 1 d . U . . .
C33 C 1.0855(10) 0.6852(8) 0.9107(5) 0.0246(19) Uani 1 1 d . U . . .
H33 H 1.141845 0.675471 0.871402 0.030 Uiso 1 1 calc R U . . .
C34 C 1.1039(11) 0.6057(8) 0.9827(6) 0.030(2) Uani 1 1 d . U . . .
H34 H 1.175030 0.542383 0.994053 0.035 Uiso 1 1 calc R U . . .
C35 C 1.0180(10) 0.6184(8) 1.0389(5) 0.0217(18) Uani 1 1 d . U . . .
C36 C 0.9196(9) 0.7134(7) 1.0243(5) 0.0178(17) Uani 1 1 d . U . . .
H36 H 0.863578 0.722787 1.063824 0.021 Uiso 1 1 calc R U . . .
C37 C 0.9022(9) 0.7948(7) 0.9524(5) 0.0184(18) Uani 1 1 d . U . . .
H37 H 0.834553 0.860345 0.942028 0.022 Uiso 1 1 calc R U . . .
O2 O 1.0414(8) 0.5332(6) 1.1079(4) 0.0288(16) Uani 1 1 d . . . . .
C38 C 0.9485(12) 0.5388(9) 1.1655(5) 0.033(2) Uani 1 1 d . . . . .
H38A H 0.953036 0.602817 1.182023 0.050 Uiso 1 1 calc R U . . .
H38B H 0.970301 0.469809 1.210001 0.050 Uiso 1 1 calc R U . . .
H38C H 0.858723 0.547511 1.143673 0.050 Uiso 1 1 calc R U . . .
C101 C 0.2596(10) 0.6764(8) 0.6581(5) 0.025(2) Uani 1 1 d . . . . .
H101 H 0.194065 0.749214 0.643695 0.030 Uiso 1 1 calc R U . . .
Cl11 Cl 0.3978(3) 0.6946(3) 0.60342(16) 0.0520(9) Uani 1 1 d . . . . .
Cl12 Cl 0.3102(3) 0.6348(3) 0.75663(15) 0.0393(7) Uani 1 1 d . . . . .
Cl13 Cl 0.1856(4) 0.5776(3) 0.6386(2) 0.0514(8) Uani 1 1 d . . . . .
C111 C 0.3990(13) 0.6873(9) 0.1475(6) 0.039(3) Uani 1 1 d . . . . .
H111 H 0.435073 0.756723 0.136131 0.046 Uiso 1 1 calc R U . . .
Cl21 Cl 0.4239(4) 0.6150(3) 0.24676(16) 0.0501(8) Uani 1 1 d . . . . .
Cl22 Cl 0.4845(5) 0.6049(2) 0.09540(18) 0.0611(11) Uani 1 1 d . . . . .
Cl23 Cl 0.2288(4) 0.7263(3) 0.11828(19) 0.0644(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C11 1.954(8) . ?
Ru1 C3 2.157(8) . ?
Ru1 C2 2.171(9) . ?
Ru1 C4 2.192(9) . ?
Ru1 C1 2.206(9) . ?
Ru1 C5 2.221(8) . ?
Ru1 C6 2.223(9) . ?
Ru1 Cl1 2.399(2) . ?
Ru1 Cl2 2.404(2) . ?
C1 C2 1.411(13) . ?
C1 C6 1.430(14) . ?
C1 C7 1.507(13) . ?
C2 C3 1.382(13) . ?
C3 C4 1.393(12) . ?
C4 C5 1.442(13) . ?
C4 C8 1.497(14) . ?
C5 C6 1.362(14) . ?
C8 C9 1.499(14) . ?
C8 C10 1.517(14) . ?
N1 C11 1.156(11) . ?
N1 C12 1.404(10) . ?
C12 C13 1.373(13) . ?
C12 C17 1.395(13) . ?
C13 C14 1.372(12) . ?
C14 C15 1.401(12) . ?
C15 O1 1.369(10) . ?
C15 C16 1.376(12) . ?
C16 C17 1.388(12) . ?
O1 C18 1.414(11) . ?
Ru2 C31 1.971(9) . ?
Ru2 C25 2.170(9) . ?
Ru2 C24 2.190(9) . ?
Ru2 C26 2.191(9) . ?
Ru2 C23 2.210(8) . ?
Ru2 C21 2.219(9) . ?
Ru2 C22 2.237(9) . ?
Ru2 Cl4 2.403(2) . ?
Ru2 Cl3 2.412(2) . ?
C21 C26 1.390(13) . ?
C21 C22 1.433(14) . ?
C21 C27 1.499(13) . ?
C22 C23 1.379(13) . ?
C23 C24 1.434(13) . ?
C24 C25 1.379(13) . ?
C24 C28 1.519(13) . ?
C25 C26 1.407(12) . ?
C28 C30 1.502(15) . ?
C28 C29 1.522(14) . ?
N2 C31 1.152(11) . ?
N2 C32 1.391(11) . ?
C32 C33 1.379(13) . ?
C32 C37 1.396(13) . ?
C33 C34 1.369(13) . ?
C34 C35 1.387(14) . ?
C35 O2 1.364(10) . ?
C35 C36 1.380(13) . ?
C36 C37 1.378(12) . ?
O2 C38 1.435(13) . ?
C101 Cl13 1.741(11) . ?
C101 Cl11 1.753(10) . ?
C101 Cl12 1.756(10) . ?
C111 Cl21 1.746(11) . ?
C111 Cl23 1.761(13) . ?
C111 Cl22 1.765(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 Ru1 C3 93.0(3) . . ?
C11 Ru1 C2 97.1(4) . . ?
C3 Ru1 C2 37.2(3) . . ?
C11 Ru1 C4 114.6(3) . . ?
C3 Ru1 C4 37.4(3) . . ?
C2 Ru1 C4 67.8(3) . . ?
C11 Ru1 C1 124.9(4) . . ?
C3 Ru1 C1 67.7(3) . . ?
C2 Ru1 C1 37.6(3) . . ?
C4 Ru1 C1 81.0(3) . . ?
C11 Ru1 C5 152.2(4) . . ?
C3 Ru1 C5 66.7(3) . . ?
C2 Ru1 C5 78.4(3) . . ?
C4 Ru1 C5 38.1(3) . . ?
C1 Ru1 C5 66.5(4) . . ?
C11 Ru1 C6 162.5(4) . . ?
C3 Ru1 C6 78.9(3) . . ?
C2 Ru1 C6 67.1(3) . . ?
C4 Ru1 C6 67.5(3) . . ?
C1 Ru1 C6 37.7(4) . . ?
C5 Ru1 C6 35.7(4) . . ?
C11 Ru1 Cl1 85.5(3) . . ?
C3 Ru1 Cl1 121.7(2) . . ?
C2 Ru1 Cl1 158.7(3) . . ?
C4 Ru1 Cl1 91.8(2) . . ?
C1 Ru1 Cl1 149.1(3) . . ?
C5 Ru1 Cl1 89.4(3) . . ?
C6 Ru1 Cl1 111.9(3) . . ?
C11 Ru1 Cl2 84.8(2) . . ?
C3 Ru1 Cl2 149.9(2) . . ?
C2 Ru1 Cl2 113.1(3) . . ?
C4 Ru1 Cl2 160.5(3) . . ?
C1 Ru1 Cl2 89.0(2) . . ?
C5 Ru1 Cl2 122.4(3) . . ?
C6 Ru1 Cl2 94.4(2) . . ?
Cl1 Ru1 Cl2 88.17(8) . . ?
C2 C1 C6 117.5(9) . . ?
C2 C1 C7 121.8(9) . . ?
C6 C1 C7 120.7(8) . . ?
C2 C1 Ru1 69.9(5) . . ?
C6 C1 Ru1 71.8(5) . . ?
C7 C1 Ru1 130.0(6) . . ?
C3 C2 C1 120.9(9) . . ?
C3 C2 Ru1 70.8(5) . . ?
C1 C2 Ru1 72.5(5) . . ?
C2 C3 C4 122.6(8) . . ?
C2 C3 Ru1 71.9(5) . . ?
C4 C3 Ru1 72.7(5) . . ?
C3 C4 C5 116.2(9) . . ?
C3 C4 C8 123.9(9) . . ?
C5 C4 C8 119.9(8) . . ?
C3 C4 Ru1 70.0(5) . . ?
C5 C4 Ru1 72.0(5) . . ?
C8 C4 Ru1 129.6(6) . . ?
C6 C5 C4 122.1(9) . . ?
C6 C5 Ru1 72.2(5) . . ?
C4 C5 Ru1 69.8(5) . . ?
C5 C6 C1 120.6(9) . . ?
C5 C6 Ru1 72.1(5) . . ?
C1 C6 Ru1 70.5(5) . . ?
C4 C8 C9 113.5(8) . . ?
C4 C8 C10 109.5(9) . . ?
C9 C8 C10 111.0(9) . . ?
C11 N1 C12 176.7(10) . . ?
N1 C11 Ru1 177.2(8) . . ?
C13 C12 C17 121.1(8) . . ?
C13 C12 N1 120.1(8) . . ?
C17 C12 N1 118.7(8) . . ?
C14 C13 C12 119.9(9) . . ?
C13 C14 C15 119.6(9) . . ?
O1 C15 C16 124.1(8) . . ?
O1 C15 C14 115.3(8) . . ?
C16 C15 C14 120.6(8) . . ?
C15 C16 C17 119.6(8) . . ?
C16 C17 C12 119.2(8) . . ?
C15 O1 C18 117.1(7) . . ?
C31 Ru2 C25 93.8(3) . . ?
C31 Ru2 C24 115.6(4) . . ?
C25 Ru2 C24 36.9(3) . . ?
C31 Ru2 C26 97.8(4) . . ?
C25 Ru2 C26 37.6(3) . . ?
C24 Ru2 C26 67.4(3) . . ?
C31 Ru2 C23 153.0(3) . . ?
C25 Ru2 C23 66.7(3) . . ?
C24 Ru2 C23 38.0(3) . . ?
C26 Ru2 C23 78.3(3) . . ?
C31 Ru2 C21 124.7(4) . . ?
C25 Ru2 C21 67.3(3) . . ?
C24 Ru2 C21 80.2(3) . . ?
C26 Ru2 C21 36.7(3) . . ?
C23 Ru2 C21 66.5(3) . . ?
C31 Ru2 C22 162.2(4) . . ?
C25 Ru2 C22 78.9(3) . . ?
C24 Ru2 C22 67.4(3) . . ?
C26 Ru2 C22 66.5(3) . . ?
C23 Ru2 C22 36.1(3) . . ?
C21 Ru2 C22 37.5(4) . . ?
C31 Ru2 Cl4 83.6(3) . . ?
C25 Ru2 Cl4 150.6(2) . . ?
C24 Ru2 Cl4 160.7(3) . . ?
C26 Ru2 Cl4 113.5(2) . . ?
C23 Ru2 Cl4 122.7(2) . . ?
C21 Ru2 Cl4 90.1(2) . . ?
C22 Ru2 Cl4 94.8(2) . . ?
C31 Ru2 Cl3 86.3(3) . . ?
C25 Ru2 Cl3 122.5(2) . . ?
C24 Ru2 Cl3 92.9(3) . . ?
C26 Ru2 Cl3 159.7(2) . . ?
C23 Ru2 Cl3 88.9(2) . . ?
C21 Ru2 Cl3 148.2(3) . . ?
C22 Ru2 Cl3 111.3(3) . . ?
Cl4 Ru2 Cl3 86.62(7) . . ?
C26 C21 C22 118.7(9) . . ?
C26 C21 C27 121.7(9) . . ?
C22 C21 C27 119.6(9) . . ?
C26 C21 Ru2 70.5(5) . . ?
C22 C21 Ru2 71.9(5) . . ?
C27 C21 Ru2 129.3(6) . . ?
C23 C22 C21 119.5(8) . . ?
C23 C22 Ru2 70.9(5) . . ?
C21 C22 Ru2 70.6(5) . . ?
C22 C23 C24 121.8(8) . . ?
C22 C23 Ru2 73.0(5) . . ?
C24 C23 Ru2 70.2(5) . . ?
C25 C24 C23 117.6(8) . . ?
C25 C24 C28 124.4(8) . . ?
C23 C24 C28 118.0(8) . . ?
C25 C24 Ru2 70.8(5) . . ?
C23 C24 Ru2 71.7(5) . . ?
C28 C24 Ru2 128.8(6) . . ?
C24 C25 C26 121.5(8) . . ?
C24 C25 Ru2 72.4(5) . . ?
C26 C25 Ru2 72.0(5) . . ?
C21 C26 C25 120.8(9) . . ?
C21 C26 Ru2 72.7(5) . . ?
C25 C26 Ru2 70.4(5) . . ?
C30 C28 C24 113.1(9) . . ?
C30 C28 C29 112.2(9) . . ?
C24 C28 C29 109.4(8) . . ?
C31 N2 C32 173.8(9) . . ?
N2 C31 Ru2 176.7(9) . . ?
C33 C32 N2 119.9(8) . . ?
C33 C32 C37 120.5(8) . . ?
N2 C32 C37 119.5(8) . . ?
C34 C33 C32 120.2(9) . . ?
C33 C34 C35 119.5(9) . . ?
O2 C35 C36 124.2(9) . . ?
O2 C35 C34 115.3(9) . . ?
C36 C35 C34 120.5(8) . . ?
C37 C36 C35 120.1(9) . . ?
C36 C37 C32 119.0(9) . . ?
C35 O2 C38 117.0(8) . . ?
Cl13 C101 Cl11 110.0(6) . . ?
Cl13 C101 Cl12 111.1(5) . . ?
Cl11 C101 Cl12 109.1(6) . . ?
Cl21 C111 Cl23 110.7(7) . . ?
Cl21 C111 Cl22 110.4(7) . . ?
Cl23 C111 Cl22 110.4(7) . . ?

_refine_diff_density_max         1.593
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.188

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4f
_database_code_depnum_ccdc_archive 'CCDC 2504600'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H32 Cl N Ru'
_chemical_formula_weight         531.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.2888(9)
_cell_length_b                   12.6570(13)
_cell_length_c                   23.549(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.116(4)
_cell_angle_gamma                90
_cell_volume                     2445.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.3755
_cell_measurement_theta_max      27.1725

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.767
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6003
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1177 (selected reflections only, before parameter refinement)
 R(int) =  0.0621 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35819
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.747
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5346
_reflns_number_gt                4935
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+10.6810P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5346
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5433(4) 0.6780(3) 0.38321(16) 0.0160(7) Uani 1 1 d . . . . .
C2 C 0.5139(5) 0.4926(3) 0.42112(16) 0.0199(8) Uani 1 1 d . . . . .
C3 C 0.6418(5) 0.4290(4) 0.44611(18) 0.0245(9) Uani 1 1 d . . . . .
C4 C 0.6021(6) 0.3316(4) 0.46759(19) 0.0300(10) Uani 1 1 d . . . . .
H4 H 0.686476 0.287005 0.485574 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4428(6) 0.2986(3) 0.4632(2) 0.0321(11) Uani 1 1 d . . . . .
H5 H 0.418079 0.231659 0.478074 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3189(6) 0.3621(4) 0.4375(2) 0.0320(10) Uani 1 1 d . . . . .
H6 H 0.209547 0.337843 0.434248 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3511(5) 0.4610(3) 0.41603(18) 0.0235(9) Uani 1 1 d . . . . .
C8 C 0.8136(6) 0.4658(4) 0.4493(2) 0.0337(11) Uani 1 1 d . . . . .
H8A H 0.838415 0.479651 0.410549 0.051 Uiso 1 1 calc R U . . .
H8B H 0.887197 0.411073 0.467479 0.051 Uiso 1 1 calc R U . . .
H8C H 0.828195 0.530765 0.472097 0.051 Uiso 1 1 calc R U . . .
C9 C 0.2164(6) 0.5335(4) 0.3888(2) 0.0370(11) Uani 1 1 d . . . . .
H9A H 0.111858 0.496152 0.385171 0.056 Uiso 1 1 calc R U . . .
H9B H 0.238618 0.555011 0.350647 0.056 Uiso 1 1 calc R U . . .
H9C H 0.211543 0.596268 0.412844 0.056 Uiso 1 1 calc R U . . .
C11 C 0.3600(5) 0.7641(3) 0.29299(17) 0.0170(8) Uani 1 1 d . . . . .
C12 C 0.2644(5) 0.7299(3) 0.25629(19) 0.0252(9) Uani 1 1 d . . . . .
C13 C 0.1532(5) 0.6859(4) 0.20861(19) 0.0283(9) Uani 1 1 d . . . . .
C14 C 0.1402(6) 0.7295(4) 0.1535(2) 0.0298(10) Uani 1 1 d . . . . .
H14 H 0.199642 0.791609 0.147148 0.036 Uiso 1 1 calc R U . . .
C15 C 0.0406(6) 0.6824(5) 0.1078(2) 0.0384(12) Uani 1 1 d . . . . .
H15 H 0.034220 0.711932 0.070473 0.046 Uiso 1 1 calc R U . . .
C16 C -0.0485(6) 0.5934(4) 0.1162(2) 0.0349(11) Uani 1 1 d . . . . .
H16 H -0.116632 0.561918 0.084938 0.042 Uiso 1 1 calc R U . . .
C17 C -0.0381(5) 0.5504(4) 0.1703(2) 0.0318(11) Uani 1 1 d . . . . .
H17 H -0.100640 0.489592 0.176264 0.038 Uiso 1 1 calc R U . . .
C18 C 0.0624(5) 0.5947(4) 0.2162(2) 0.0287(10) Uani 1 1 d . . . . .
H18 H 0.069959 0.562944 0.252997 0.034 Uiso 1 1 calc R U . . .
C101 C 0.6892(5) 0.9543(3) 0.39866(17) 0.0206(8) Uani 1 1 d . . . . .
C102 C 0.5893(5) 0.9972(3) 0.34855(18) 0.0213(8) Uani 1 1 d . . . . .
C103 C 0.5945(5) 0.9515(3) 0.29460(18) 0.0241(9) Uani 1 1 d . . . . .
C104 C 0.6926(5) 0.8596(4) 0.28924(18) 0.0254(9) Uani 1 1 d . . . . .
C105 C 0.7915(5) 0.8178(3) 0.33872(18) 0.0221(8) Uani 1 1 d . . . . .
C106 C 0.7935(5) 0.8686(3) 0.39343(17) 0.0203(8) Uani 1 1 d . . . . .
C111 C 0.6806(6) 1.0050(4) 0.45603(19) 0.0299(10) Uani 1 1 d . . . . .
H11A H 0.699976 0.951430 0.486276 0.045 Uiso 1 1 calc R U . . .
H11B H 0.572417 1.036198 0.456130 0.045 Uiso 1 1 calc R U . . .
H11C H 0.763708 1.060330 0.463001 0.045 Uiso 1 1 calc R U . . .
C112 C 0.4816(6) 1.0897(4) 0.3558(2) 0.0330(11) Uani 1 1 d . . . . .
H11D H 0.414462 1.105540 0.319135 0.049 Uiso 1 1 calc R U . . .
H11E H 0.548959 1.151233 0.368465 0.049 Uiso 1 1 calc R U . . .
H11F H 0.410918 1.072821 0.384591 0.049 Uiso 1 1 calc R U . . .
C113 C 0.4905(7) 0.9950(4) 0.2415(2) 0.0377(12) Uani 1 1 d . . . . .
H11G H 0.381364 1.011464 0.250406 0.057 Uiso 1 1 calc R U . . .
H11H H 0.482327 0.942263 0.210732 0.057 Uiso 1 1 calc R U . . .
H11I H 0.540884 1.059455 0.228953 0.057 Uiso 1 1 calc R U . . .
C114 C 0.7033(7) 0.8135(4) 0.2307(2) 0.0399(12) Uani 1 1 d . . . . .
H11J H 0.763451 0.746614 0.234985 0.060 Uiso 1 1 calc R U . . .
H11K H 0.760146 0.863142 0.208471 0.060 Uiso 1 1 calc R U . . .
H11L H 0.593212 0.800700 0.210581 0.060 Uiso 1 1 calc R U . . .
C115 C 0.8994(6) 0.7227(4) 0.3351(2) 0.0351(11) Uani 1 1 d . . . . .
H11M H 0.855793 0.679718 0.301789 0.053 Uiso 1 1 calc R U . . .
H11N H 0.902721 0.680441 0.370082 0.053 Uiso 1 1 calc R U . . .
H11O H 1.009830 0.746162 0.330934 0.053 Uiso 1 1 calc R U . . .
C116 C 0.9060(5) 0.8278(4) 0.4451(2) 0.0339(11) Uani 1 1 d . . . . .
H11P H 0.907366 0.877767 0.476935 0.051 Uiso 1 1 calc R U . . .
H11Q H 1.016435 0.820188 0.435279 0.051 Uiso 1 1 calc R U . . .
H11R H 0.866949 0.758921 0.456497 0.051 Uiso 1 1 calc R U . . .
Cl1 Cl 0.32576(12) 0.85482(8) 0.41290(4) 0.0207(2) Uani 1 1 d . . . . .
N1 N 0.5493(4) 0.5931(3) 0.40110(14) 0.0211(7) Uani 1 1 d . . . . .
Ru1 Ru 0.53507(4) 0.82067(2) 0.35410(2) 0.01368(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.152(5) . ?
C1 Ru1 1.929(4) . ?
C2 C3 1.394(6) . ?
C2 C7 1.397(6) . ?
C2 N1 1.402(5) . ?
C3 C4 1.390(6) . ?
C3 C8 1.490(6) . ?
C4 C5 1.375(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(6) . ?
C6 H6 0.9500 . ?
C7 C9 1.516(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.170(6) . ?
C11 Ru1 2.025(4) . ?
C12 C13 1.459(6) . ?
C13 C14 1.401(6) . ?
C13 C18 1.404(7) . ?
C14 C15 1.394(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C101 C106 1.403(6) . ?
C101 C102 1.448(6) . ?
C101 C111 1.507(6) . ?
C101 Ru1 2.284(4) . ?
C102 C103 1.402(6) . ?
C102 C112 1.496(6) . ?
C102 Ru1 2.287(4) . ?
C103 C104 1.435(6) . ?
C103 C113 1.519(6) . ?
C103 Ru1 2.268(4) . ?
C104 C105 1.428(6) . ?
C104 C114 1.512(6) . ?
C104 Ru1 2.201(4) . ?
C105 C106 1.438(6) . ?
C105 C115 1.509(6) . ?
C105 Ru1 2.206(4) . ?
C106 C116 1.516(6) . ?
C106 Ru1 2.292(4) . ?
C111 H11A 0.9800 . ?
C111 H11B 0.9800 . ?
C111 H11C 0.9800 . ?
C112 H11D 0.9800 . ?
C112 H11E 0.9800 . ?
C112 H11F 0.9800 . ?
C113 H11G 0.9800 . ?
C113 H11H 0.9800 . ?
C113 H11I 0.9800 . ?
C114 H11J 0.9800 . ?
C114 H11K 0.9800 . ?
C114 H11L 0.9800 . ?
C115 H11M 0.9800 . ?
C115 H11N 0.9800 . ?
C115 H11O 0.9800 . ?
C116 H11P 0.9800 . ?
C116 H11Q 0.9800 . ?
C116 H11R 0.9800 . ?
Cl1 Ru1 2.4067(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 Ru1 179.3(4) . . ?
C3 C2 C7 122.6(4) . . ?
C3 C2 N1 118.9(4) . . ?
C7 C2 N1 118.5(4) . . ?
C4 C3 C2 117.5(4) . . ?
C4 C3 C8 122.1(4) . . ?
C2 C3 C8 120.4(4) . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 117.4(4) . . ?
C6 C7 C9 122.1(4) . . ?
C2 C7 C9 120.5(4) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C11 Ru1 176.9(4) . . ?
C11 C12 C13 176.6(5) . . ?
C14 C13 C18 118.0(4) . . ?
C14 C13 C12 121.4(4) . . ?
C18 C13 C12 120.5(4) . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.7(5) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.4(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.9(5) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 120.5(5) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C106 C101 C102 120.5(4) . . ?
C106 C101 C111 121.1(4) . . ?
C102 C101 C111 118.5(4) . . ?
C106 C101 Ru1 72.5(2) . . ?
C102 C101 Ru1 71.6(2) . . ?
C111 C101 Ru1 129.3(3) . . ?
C103 C102 C101 119.8(4) . . ?
C103 C102 C112 121.4(4) . . ?
C101 C102 C112 118.8(4) . . ?
C103 C102 Ru1 71.3(2) . . ?
C101 C102 Ru1 71.4(2) . . ?
C112 C102 Ru1 129.2(3) . . ?
C102 C103 C104 120.3(4) . . ?
C102 C103 C113 120.7(4) . . ?
C104 C103 C113 118.9(4) . . ?
C102 C103 Ru1 72.8(2) . . ?
C104 C103 Ru1 68.7(2) . . ?
C113 C103 Ru1 128.8(3) . . ?
C105 C104 C103 119.7(4) . . ?
C105 C104 C114 120.0(4) . . ?
C103 C104 C114 120.0(4) . . ?
C105 C104 Ru1 71.3(2) . . ?
C103 C104 Ru1 73.8(2) . . ?
C114 C104 Ru1 131.6(3) . . ?
C104 C105 C106 119.9(4) . . ?
C104 C105 C115 121.7(4) . . ?
C106 C105 C115 118.4(4) . . ?
C104 C105 Ru1 70.9(2) . . ?
C106 C105 Ru1 74.6(2) . . ?
C115 C105 Ru1 128.0(3) . . ?
C101 C106 C105 119.7(4) . . ?
C101 C106 C116 120.7(4) . . ?
C105 C106 C116 119.7(4) . . ?
C101 C106 Ru1 71.8(2) . . ?
C105 C106 Ru1 68.1(2) . . ?
C116 C106 Ru1 131.9(3) . . ?
C101 C111 H11A 109.5 . . ?
C101 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
C101 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
C102 C112 H11D 109.5 . . ?
C102 C112 H11E 109.5 . . ?
H11D C112 H11E 109.5 . . ?
C102 C112 H11F 109.5 . . ?
H11D C112 H11F 109.5 . . ?
H11E C112 H11F 109.5 . . ?
C103 C113 H11G 109.5 . . ?
C103 C113 H11H 109.5 . . ?
H11G C113 H11H 109.5 . . ?
C103 C113 H11I 109.5 . . ?
H11G C113 H11I 109.5 . . ?
H11H C113 H11I 109.5 . . ?
C104 C114 H11J 109.5 . . ?
C104 C114 H11K 109.5 . . ?
H11J C114 H11K 109.5 . . ?
C104 C114 H11L 109.5 . . ?
H11J C114 H11L 109.5 . . ?
H11K C114 H11L 109.5 . . ?
C105 C115 H11M 109.5 . . ?
C105 C115 H11N 109.5 . . ?
H11M C115 H11N 109.5 . . ?
C105 C115 H11O 109.5 . . ?
H11M C115 H11O 109.5 . . ?
H11N C115 H11O 109.5 . . ?
C106 C116 H11P 109.5 . . ?
C106 C116 H11Q 109.5 . . ?
H11P C116 H11Q 109.5 . . ?
C106 C116 H11R 109.5 . . ?
H11P C116 H11R 109.5 . . ?
H11Q C116 H11R 109.5 . . ?
C1 N1 C2 165.6(4) . . ?
C1 Ru1 C11 84.70(15) . . ?
C1 Ru1 C104 117.48(17) . . ?
C11 Ru1 C104 91.24(16) . . ?
C1 Ru1 C105 93.22(16) . . ?
C11 Ru1 C105 119.19(16) . . ?
C104 Ru1 C105 37.83(16) . . ?
C1 Ru1 C103 154.58(16) . . ?
C11 Ru1 C103 90.87(15) . . ?
C104 Ru1 C103 37.43(17) . . ?
C105 Ru1 C103 67.21(16) . . ?
C1 Ru1 C101 122.71(16) . . ?
C11 Ru1 C101 152.47(15) . . ?
C104 Ru1 C101 78.75(15) . . ?
C105 Ru1 C101 66.31(15) . . ?
C103 Ru1 C101 65.60(15) . . ?
C1 Ru1 C102 159.64(15) . . ?
C11 Ru1 C102 115.58(15) . . ?
C104 Ru1 C102 66.48(16) . . ?
C105 Ru1 C102 78.77(15) . . ?
C103 Ru1 C102 35.86(15) . . ?
C101 Ru1 C102 36.95(15) . . ?
C1 Ru1 C106 96.88(15) . . ?
C11 Ru1 C106 156.32(15) . . ?
C104 Ru1 C106 66.99(15) . . ?
C105 Ru1 C106 37.23(15) . . ?
C103 Ru1 C106 77.56(15) . . ?
C101 Ru1 C106 35.71(15) . . ?
C102 Ru1 C106 65.45(15) . . ?
C1 Ru1 Cl1 87.47(11) . . ?
C11 Ru1 Cl1 88.28(11) . . ?
C104 Ru1 Cl1 154.90(13) . . ?
C105 Ru1 Cl1 152.48(11) . . ?
C103 Ru1 Cl1 117.47(12) . . ?
C101 Ru1 Cl1 90.27(10) . . ?
C102 Ru1 Cl1 91.19(11) . . ?
C106 Ru1 Cl1 115.37(11) . . ?

_refine_diff_density_max         1.034
_refine_diff_density_min         -1.626
_refine_diff_density_rms         0.110

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1c
_database_code_depnum_ccdc_archive 'CCDC 2504594'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Cl2 N Ru'
_chemical_formula_weight         437.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.1021(6)
_cell_length_b                   11.0511(8)
_cell_length_c                   18.3886(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1849.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      2.215
_cell_measurement_theta_max      27.143

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.135
_shelx_estimated_absorpt_T_min   0.866
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3985
_exptl_absorpt_correction_T_max  0.5628
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1417 (selected reflections only, before parameter refinement)
 R(int) =  0.0727 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22191
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4024
_reflns_number_gt                3916
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²+5.7420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4024
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.240
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.60639(5) 0.39017(4) 0.42839(3) 0.00929(14) Uani 1 1 d . . . . .
Cl1 Cl 0.3940(2) 0.51930(14) 0.43624(9) 0.0178(3) Uani 1 1 d . . . . .
Cl2 Cl 0.62634(17) 0.40641(15) 0.55821(8) 0.0157(3) Uani 1 1 d . . . . .
N1 N 0.7831(6) 0.6319(5) 0.4266(4) 0.0171(12) Uani 1 1 d . . . . .
C1 C 0.7187(7) 0.5424(6) 0.4262(4) 0.0127(13) Uani 1 1 d . . . . .
C2 C 0.8599(7) 0.7459(6) 0.4280(4) 0.0149(13) Uani 1 1 d . . . . .
H2 H 0.808027 0.800438 0.462996 0.018 Uiso 1 1 calc R U . . .
C3 C 1.0168(8) 0.7261(7) 0.4560(4) 0.0187(15) Uani 1 1 d . . . . .
H3A H 1.013176 0.693732 0.505638 0.028 Uiso 1 1 calc R U . . .
H3B H 1.069710 0.803317 0.456104 0.028 Uiso 1 1 calc R U . . .
H3C H 1.067784 0.668523 0.424313 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8567(7) 0.8053(6) 0.3537(4) 0.0142(14) Uani 1 1 d . . . . .
C5 C 0.8490(8) 0.9301(7) 0.3497(4) 0.0198(16) Uani 1 1 d . . . . .
H5 H 0.843481 0.976484 0.393075 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8493(9) 0.9886(7) 0.2823(5) 0.0239(18) Uani 1 1 d . . . . .
H6 H 0.842856 1.074352 0.279952 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8587(8) 0.9220(8) 0.2199(4) 0.0239(18) Uani 1 1 d . . . . .
H7 H 0.859268 0.961875 0.174128 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8676(8) 0.7969(7) 0.2227(4) 0.0215(17) Uani 1 1 d . . . . .
H8 H 0.873337 0.751302 0.179052 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8681(8) 0.7379(7) 0.2902(4) 0.0197(15) Uani 1 1 d . . . . .
H9 H 0.876159 0.652250 0.292456 0.024 Uiso 1 1 calc R U . . .
C11 C 0.5844(8) 0.1852(5) 0.4378(4) 0.0157(14) Uani 1 1 d . . . . .
C12 C 0.7325(8) 0.2211(6) 0.4245(4) 0.0141(13) Uani 1 1 d . . . . .
H12 H 0.809083 0.205212 0.462339 0.017 Uiso 1 1 calc R U . . .
C13 C 0.7674(8) 0.2925(6) 0.3644(4) 0.0130(14) Uani 1 1 d . . . . .
H13 H 0.868980 0.326168 0.360288 0.016 Uiso 1 1 calc R U . . .
C14 C 0.6569(8) 0.3355(6) 0.3157(4) 0.0131(14) Uani 1 1 d . . . . .
C15 C 0.5101(8) 0.3069(6) 0.3327(4) 0.0133(14) Uani 1 1 d . . . . .
H15 H 0.429173 0.350004 0.306608 0.016 Uiso 1 1 calc R U . . .
C16 C 0.4744(8) 0.2304(7) 0.3919(4) 0.0152(14) Uani 1 1 d . . . . .
H16 H 0.369447 0.223852 0.407505 0.018 Uiso 1 1 calc R U . . .
C17 C 0.5483(8) 0.1078(7) 0.5025(4) 0.0201(14) Uani 1 1 d . . . . .
H17A H 0.442718 0.090350 0.502873 0.030 Uiso 1 1 calc R U . . .
H17B H 0.575123 0.150762 0.547151 0.030 Uiso 1 1 calc R U . . .
H17C H 0.603379 0.031787 0.499549 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6986(8) 0.4081(7) 0.2487(4) 0.0188(16) Uani 1 1 d . . . . .
H18 H 0.796988 0.445200 0.258152 0.023 Uiso 1 1 calc R U . . .
C19 C 0.7153(12) 0.3227(8) 0.1841(4) 0.034(2) Uani 1 1 d . . . . .
H19A H 0.790710 0.262071 0.194956 0.052 Uiso 1 1 calc R U . . .
H19B H 0.744475 0.369115 0.140996 0.052 Uiso 1 1 calc R U . . .
H19C H 0.621472 0.282141 0.174684 0.052 Uiso 1 1 calc R U . . .
C20 C 0.5924(11) 0.5103(8) 0.2322(5) 0.0300(19) Uani 1 1 d . . . . .
H20A H 0.498290 0.476528 0.216091 0.045 Uiso 1 1 calc R U . . .
H20B H 0.633199 0.561522 0.193607 0.045 Uiso 1 1 calc R U . . .
H20C H 0.577095 0.558971 0.276071 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C1 1.969(6) . ?
Ru1 C13 2.168(7) . ?
Ru1 C15 2.170(7) . ?
Ru1 C12 2.194(6) . ?
Ru1 C14 2.207(7) . ?
Ru1 C16 2.239(7) . ?
Ru1 C11 2.280(6) . ?
Ru1 Cl2 2.4008(15) . ?
Ru1 Cl1 2.4074(17) . ?
N1 C1 1.150(8) . ?
N1 C2 1.441(8) . ?
C2 C4 1.517(10) . ?
C2 C3 1.534(9) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.383(11) . ?
C4 C9 1.389(10) . ?
C5 C6 1.397(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.366(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(11) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C16 1.402(10) . ?
C11 C12 1.426(10) . ?
C11 C17 1.501(9) . ?
C12 C13 1.396(10) . ?
C12 H12 1.0000 . ?
C13 C14 1.427(10) . ?
C13 H13 1.0000 . ?
C14 C15 1.409(10) . ?
C14 C18 1.518(9) . ?
C15 C16 1.415(10) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.518(11) . ?
C18 C19 1.525(11) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ru1 C13 93.6(3) . . ?
C1 Ru1 C15 123.7(3) . . ?
C13 Ru1 C15 67.8(3) . . ?
C1 Ru1 C12 117.1(2) . . ?
C13 Ru1 C12 37.3(3) . . ?
C15 Ru1 C12 79.9(3) . . ?
C1 Ru1 C14 96.1(3) . . ?
C13 Ru1 C14 38.1(3) . . ?
C15 Ru1 C14 37.5(3) . . ?
C12 Ru1 C14 68.1(3) . . ?
C1 Ru1 C16 161.1(3) . . ?
C13 Ru1 C16 78.9(3) . . ?
C15 Ru1 C16 37.4(3) . . ?
C12 Ru1 C16 66.4(2) . . ?
C14 Ru1 C16 67.3(3) . . ?
C1 Ru1 C11 153.6(3) . . ?
C13 Ru1 C11 66.8(3) . . ?
C15 Ru1 C11 66.7(3) . . ?
C12 Ru1 C11 37.1(2) . . ?
C14 Ru1 C11 79.5(3) . . ?
C16 Ru1 C11 36.1(3) . . ?
C1 Ru1 Cl2 85.3(2) . . ?
C13 Ru1 Cl2 121.75(19) . . ?
C15 Ru1 Cl2 150.2(2) . . ?
C12 Ru1 Cl2 93.2(2) . . ?
C14 Ru1 Cl2 159.77(18) . . ?
C16 Ru1 Cl2 113.4(2) . . ?
C11 Ru1 Cl2 90.30(18) . . ?
C1 Ru1 Cl1 84.94(19) . . ?
C13 Ru1 Cl1 150.54(19) . . ?
C15 Ru1 Cl1 88.60(19) . . ?
C12 Ru1 Cl1 157.95(18) . . ?
C14 Ru1 Cl1 112.71(19) . . ?
C16 Ru1 Cl1 93.12(18) . . ?
C11 Ru1 Cl1 120.91(19) . . ?
Cl2 Ru1 Cl1 87.52(6) . . ?
C1 N1 C2 178.2(7) . . ?
N1 C1 Ru1 178.3(7) . . ?
N1 C2 C4 110.6(6) . . ?
N1 C2 C3 109.4(5) . . ?
C4 C2 C3 112.5(6) . . ?
N1 C2 H2 108.0 . . ?
C4 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 119.6(7) . . ?
C5 C4 C2 118.7(7) . . ?
C9 C4 C2 121.6(7) . . ?
C4 C5 C6 120.6(7) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.7(7) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.6(7) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.9(7) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 119.6(7) . . ?
C4 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C16 C11 C12 118.2(7) . . ?
C16 C11 C17 121.6(6) . . ?
C12 C11 C17 120.1(7) . . ?
C16 C11 Ru1 70.3(4) . . ?
C12 C11 Ru1 68.2(3) . . ?
C17 C11 Ru1 130.2(5) . . ?
C13 C12 C11 120.5(7) . . ?
C13 C12 Ru1 70.3(4) . . ?
C11 C12 Ru1 74.7(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
Ru1 C12 H12 119.4 . . ?
C12 C13 C14 121.7(6) . . ?
C12 C13 Ru1 72.4(4) . . ?
C14 C13 Ru1 72.4(4) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
Ru1 C13 H13 118.7 . . ?
C15 C14 C13 117.0(6) . . ?
C15 C14 C18 122.4(6) . . ?
C13 C14 C18 120.6(6) . . ?
C15 C14 Ru1 69.8(4) . . ?
C13 C14 Ru1 69.5(4) . . ?
C18 C14 Ru1 132.0(5) . . ?
C14 C15 C16 121.5(7) . . ?
C14 C15 Ru1 72.6(4) . . ?
C16 C15 Ru1 73.9(4) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
Ru1 C15 H15 119.0 . . ?
C11 C16 C15 120.8(6) . . ?
C11 C16 Ru1 73.5(4) . . ?
C15 C16 Ru1 68.7(4) . . ?
C11 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
Ru1 C16 H16 118.9 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C18 C14 113.4(6) . . ?
C20 C18 C19 111.6(7) . . ?
C14 C18 C19 109.3(6) . . ?
C20 C18 H18 107.4 . . ?
C14 C18 H18 107.4 . . ?
C19 C18 H18 107.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         1.247
_refine_diff_density_min         -1.127
_refine_diff_density_rms         0.150

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4b
_database_code_depnum_ccdc_archive 'CCDC 2504599'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H34 Cl N Ru'
_chemical_formula_weight         509.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5945(4)
_cell_length_b                   12.2445(6)
_cell_length_c                   25.2295(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.324(2)
_cell_angle_gamma                90
_cell_volume                     2345.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.784
_cell_measurement_theta_max      36.869

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.796
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2585
_exptl_absorpt_correction_T_max  0.4389
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1560 (selected reflections only, before parameter refinement)
 R(int) =  0.0680 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28581
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.615
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5623
_reflns_number_gt                5070
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0228P)²+6.7385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5623
_refine_ls_number_parameters     277
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.39640(9) 0.80623(6) 0.44453(3) 0.01535(14) Uani 1 1 d . . . . .
N1 N 0.6065(3) 0.5160(2) 0.43701(10) 0.0158(5) Uani 1 1 d . . . . .
Ru1 Ru 0.65803(3) 0.75309(2) 0.39886(2) 0.01019(7) Uani 1 1 d . . . . .
C1 C 0.6229(4) 0.6053(2) 0.42312(10) 0.0118(5) Uani 1 1 d . . . . .
C2 C 0.5920(4) 0.3992(2) 0.44430(12) 0.0161(6) Uani 1 1 d . . . . .
H2 H 0.633117 0.380090 0.481078 0.019 Uiso 1 1 calc R U . . .
C3 C 0.4002(4) 0.3645(3) 0.43676(13) 0.0222(7) Uani 1 1 d . . . . .
H3A H 0.388298 0.287101 0.447498 0.027 Uiso 1 1 calc R U . . .
H3B H 0.326106 0.408961 0.460241 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3333(4) 0.3773(3) 0.37977(13) 0.0230(7) Uani 1 1 d . . . . .
H4A H 0.331530 0.455668 0.370147 0.028 Uiso 1 1 calc R U . . .
H4B H 0.211396 0.349070 0.376498 0.028 Uiso 1 1 calc R U . . .
C5 C 0.4509(5) 0.3152(3) 0.34188(14) 0.0291(8) Uani 1 1 d . . . . .
H5A H 0.446396 0.236151 0.349878 0.035 Uiso 1 1 calc R U . . .
H5B H 0.407546 0.326129 0.304950 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6396(5) 0.3554(3) 0.34739(13) 0.0288(8) Uani 1 1 d . . . . .
H6A H 0.644952 0.433287 0.337001 0.035 Uiso 1 1 calc R U . . .
H6B H 0.714862 0.313404 0.323193 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7100(5) 0.3425(3) 0.40456(13) 0.0233(7) Uani 1 1 d . . . . .
H7A H 0.718102 0.263852 0.413365 0.028 Uiso 1 1 calc R U . . .
H7B H 0.830082 0.373781 0.407435 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5122(4) 0.7017(2) 0.33568(11) 0.0135(5) Uani 1 1 d . . . . .
C12 C 0.4462(4) 0.6649(2) 0.29547(12) 0.0173(6) Uani 1 1 d . . . . .
C13 C 0.3902(4) 0.6175(2) 0.24553(12) 0.0155(6) Uani 1 1 d . . . . .
C14 C 0.4455(4) 0.6625(3) 0.19770(12) 0.0205(6) Uani 1 1 d . . . . .
H14 H 0.509751 0.729069 0.198028 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4075(4) 0.6111(3) 0.14995(13) 0.0252(7) Uani 1 1 d . . . . .
H15 H 0.446896 0.642542 0.117909 0.030 Uiso 1 1 calc R U . . .
C16 C 0.3134(4) 0.5149(3) 0.14819(13) 0.0244(7) Uani 1 1 d . . . . .
H16 H 0.290500 0.479188 0.115313 0.029 Uiso 1 1 calc R U . . .
C17 C 0.2524(4) 0.4707(3) 0.19498(14) 0.0240(7) Uani 1 1 d . . . . .
H17 H 0.185628 0.405117 0.194108 0.029 Uiso 1 1 calc R U . . .
C18 C 0.2887(4) 0.5220(3) 0.24303(13) 0.0197(6) Uani 1 1 d . . . . .
H18 H 0.244066 0.491962 0.274723 0.024 Uiso 1 1 calc R U . . .
C101 C 0.9450(4) 0.7281(2) 0.39616(12) 0.0142(6) Uani 1 1 d . . . . .
C102 C 0.9151(4) 0.7828(2) 0.44549(12) 0.0143(5) Uani 1 1 d . . . . .
C103 C 0.8163(4) 0.8797(2) 0.44600(12) 0.0145(6) Uani 1 1 d . . . . .
C104 C 0.7557(4) 0.9290(2) 0.39634(12) 0.0155(6) Uani 1 1 d . . . . .
C105 C 0.7937(4) 0.8795(2) 0.34760(12) 0.0153(6) Uani 1 1 d . . . . .
C106 C 0.8842(4) 0.7758(2) 0.34727(12) 0.0148(6) Uani 1 1 d . . . . .
C111 C 1.0478(4) 0.6227(3) 0.39507(14) 0.0212(6) Uani 1 1 d . . . . .
H11A H 1.005032 0.577628 0.365361 0.032 Uiso 1 1 calc R U . . .
H11B H 1.031993 0.583157 0.428401 0.032 Uiso 1 1 calc R U . . .
H11C H 1.173024 0.638800 0.390743 0.032 Uiso 1 1 calc R U . . .
C112 C 0.9891(4) 0.7329(3) 0.49625(12) 0.0217(7) Uani 1 1 d . . . . .
H11D H 1.018105 0.791083 0.521661 0.033 Uiso 1 1 calc DR U . . .
H11E H 1.095707 0.691319 0.488528 0.033 Uiso 1 1 calc R U . . .
H11F H 0.901254 0.684064 0.511398 0.033 Uiso 1 1 calc R U . . .
C113 C 0.7693(4) 0.9352(3) 0.49729(13) 0.0241(7) Uani 1 1 d . . . . .
H11G H 0.814243 0.891906 0.527332 0.036 Uiso 1 1 calc DR U . . .
H11H H 0.640949 0.941569 0.499240 0.036 Uiso 1 1 calc DR U . . .
H11I H 0.822152 1.008213 0.498549 0.036 Uiso 1 1 calc R U . . .
C114 C 0.6508(4) 1.0333(3) 0.39874(15) 0.0249(7) Uani 1 1 d . . . . .
H11J H 0.551502 1.029529 0.373297 0.037 Uiso 1 1 calc DR U . . .
H11K H 0.726382 1.095237 0.389904 0.037 Uiso 1 1 calc R U . . .
H11L H 0.606224 1.042945 0.434586 0.037 Uiso 1 1 calc DR U . . .
C115 C 0.7371(5) 0.9292(3) 0.29540(13) 0.0240(7) Uani 1 1 d . . . . .
H11M H 0.671990 0.996912 0.301787 0.036 Uiso 1 1 calc DR U . . .
H11N H 0.661075 0.877765 0.275847 0.036 Uiso 1 1 calc R U . . .
H11O H 0.841200 0.945440 0.274566 0.036 Uiso 1 1 calc R U . . .
C116 C 0.9251(5) 0.7207(3) 0.29542(13) 0.0243(7) Uani 1 1 d . . . . .
H11P H 1.052574 0.721811 0.290207 0.036 Uiso 1 1 calc R U . . .
H11Q H 0.865439 0.759636 0.266211 0.036 Uiso 1 1 calc R U . . .
H11R H 0.883841 0.644884 0.296192 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 Ru1 2.4093(7) . ?
N1 C1 1.156(4) . ?
N1 C2 1.446(4) . ?
Ru1 C1 1.931(3) . ?
Ru1 C11 2.020(3) . ?
Ru1 C106 2.197(3) . ?
Ru1 C101 2.204(3) . ?
Ru1 C105 2.279(3) . ?
Ru1 C103 2.279(3) . ?
Ru1 C104 2.280(3) . ?
Ru1 C102 2.285(3) . ?
C2 C3 1.525(4) . ?
C2 C7 1.527(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.522(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.526(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.518(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.535(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 C12 1.208(4) . ?
C12 C13 1.443(4) . ?
C13 C18 1.400(4) . ?
C13 C14 1.400(4) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C101 C106 1.431(4) . ?
C101 C102 1.436(4) . ?
C101 C111 1.509(4) . ?
C102 C103 1.404(4) . ?
C102 C112 1.515(4) . ?
C103 C104 1.456(4) . ?
C103 C113 1.512(4) . ?
C104 C105 1.407(4) . ?
C104 C114 1.507(4) . ?
C105 C106 1.445(4) . ?
C105 C115 1.505(4) . ?
C106 C116 1.510(4) . ?
C111 H11A 0.9800 . ?
C111 H11B 0.9800 . ?
C111 H11C 0.9800 . ?
C112 H11D 0.9800 . ?
C112 H11E 0.9800 . ?
C112 H11F 0.9800 . ?
C113 H11G 0.9800 . ?
C113 H11H 0.9800 . ?
C113 H11I 0.9800 . ?
C114 H11J 0.9800 . ?
C114 H11K 0.9800 . ?
C114 H11L 0.9800 . ?
C115 H11M 0.9800 . ?
C115 H11N 0.9800 . ?
C115 H11O 0.9800 . ?
C116 H11P 0.9800 . ?
C116 H11Q 0.9800 . ?
C116 H11R 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 169.4(3) . . ?
C1 Ru1 C11 83.15(11) . . ?
C1 Ru1 C106 114.96(11) . . ?
C11 Ru1 C106 89.64(11) . . ?
C1 Ru1 C101 91.37(11) . . ?
C11 Ru1 C101 117.18(11) . . ?
C106 Ru1 C101 37.96(11) . . ?
C1 Ru1 C105 152.16(11) . . ?
C11 Ru1 C105 90.60(11) . . ?
C106 Ru1 C105 37.61(11) . . ?
C101 Ru1 C105 67.42(11) . . ?
C1 Ru1 C103 123.17(11) . . ?
C11 Ru1 C103 153.68(11) . . ?
C106 Ru1 C103 79.23(11) . . ?
C101 Ru1 C103 66.44(11) . . ?
C105 Ru1 C103 66.06(11) . . ?
C1 Ru1 C104 160.38(11) . . ?
C11 Ru1 C104 116.43(11) . . ?
C106 Ru1 C104 66.71(11) . . ?
C101 Ru1 C104 78.90(11) . . ?
C105 Ru1 C104 35.96(11) . . ?
C103 Ru1 C104 37.25(11) . . ?
C1 Ru1 C102 96.25(11) . . ?
C11 Ru1 C102 154.41(11) . . ?
C106 Ru1 C102 67.31(11) . . ?
C101 Ru1 C102 37.25(10) . . ?
C105 Ru1 C102 77.98(11) . . ?
C103 Ru1 C102 35.82(10) . . ?
C104 Ru1 C102 65.74(11) . . ?
C1 Ru1 Cl1 88.85(8) . . ?
C11 Ru1 Cl1 91.06(8) . . ?
C106 Ru1 Cl1 156.08(8) . . ?
C101 Ru1 Cl1 151.58(8) . . ?
C105 Ru1 Cl1 118.47(8) . . ?
C103 Ru1 Cl1 89.86(7) . . ?
C104 Ru1 Cl1 91.75(8) . . ?
C102 Ru1 Cl1 114.53(8) . . ?
N1 C1 Ru1 178.0(3) . . ?
N1 C2 C3 109.6(3) . . ?
N1 C2 C7 108.6(2) . . ?
C3 C2 C7 111.4(3) . . ?
N1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C7 C2 H2 109.1 . . ?
C4 C3 C2 112.7(3) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C5 110.7(3) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 110.3(3) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 111.1(3) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C2 C7 C6 111.9(3) . . ?
C2 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C2 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C12 C11 Ru1 171.1(3) . . ?
C11 C12 C13 172.6(3) . . ?
C18 C13 C14 117.8(3) . . ?
C18 C13 C12 121.8(3) . . ?
C14 C13 C12 120.4(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C106 C101 C102 120.2(3) . . ?
C106 C101 C111 119.3(3) . . ?
C102 C101 C111 120.5(3) . . ?
C106 C101 Ru1 70.76(16) . . ?
C102 C101 Ru1 74.46(16) . . ?
C111 C101 Ru1 129.2(2) . . ?
C103 C102 C101 119.8(3) . . ?
C103 C102 C112 121.4(3) . . ?
C101 C102 C112 118.8(3) . . ?
C103 C102 Ru1 71.85(16) . . ?
C101 C102 Ru1 68.29(16) . . ?
C112 C102 Ru1 131.8(2) . . ?
C102 C103 C104 120.1(3) . . ?
C102 C103 C113 121.7(3) . . ?
C104 C103 C113 118.3(3) . . ?
C102 C103 Ru1 72.32(17) . . ?
C104 C103 Ru1 71.40(16) . . ?
C113 C103 Ru1 128.3(2) . . ?
C105 C104 C103 120.4(3) . . ?
C105 C104 C114 121.3(3) . . ?
C103 C104 C114 118.3(3) . . ?
C105 C104 Ru1 71.97(17) . . ?
C103 C104 Ru1 71.35(16) . . ?
C114 C104 Ru1 128.8(2) . . ?
C104 C105 C106 119.4(3) . . ?
C104 C105 C115 122.0(3) . . ?
C106 C105 C115 118.5(3) . . ?
C104 C105 Ru1 72.07(16) . . ?
C106 C105 Ru1 68.13(15) . . ?
C115 C105 Ru1 130.4(2) . . ?
C101 C106 C105 119.8(3) . . ?
C101 C106 C116 119.7(3) . . ?
C105 C106 C116 120.3(3) . . ?
C101 C106 Ru1 71.28(16) . . ?
C105 C106 Ru1 74.26(16) . . ?
C116 C106 Ru1 129.5(2) . . ?
C101 C111 H11A 109.5 . . ?
C101 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
C101 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
C102 C112 H11D 109.5 . . ?
C102 C112 H11E 109.5 . . ?
H11D C112 H11E 109.5 . . ?
C102 C112 H11F 109.5 . . ?
H11D C112 H11F 109.5 . . ?
H11E C112 H11F 109.5 . . ?
C103 C113 H11G 109.5 . . ?
C103 C113 H11H 109.5 . . ?
H11G C113 H11H 109.5 . . ?
C103 C113 H11I 109.5 . . ?
H11G C113 H11I 109.5 . . ?
H11H C113 H11I 109.5 . . ?
C104 C114 H11J 109.5 . . ?
C104 C114 H11K 109.5 . . ?
H11J C114 H11K 109.5 . . ?
C104 C114 H11L 109.5 . . ?
H11J C114 H11L 109.5 . . ?
H11K C114 H11L 109.5 . . ?
C105 C115 H11M 109.5 . . ?
C105 C115 H11N 109.5 . . ?
H11M C115 H11N 109.5 . . ?
C105 C115 H11O 109.5 . . ?
H11M C115 H11O 109.5 . . ?
H11N C115 H11O 109.5 . . ?
C106 C116 H11P 109.5 . . ?
C106 C116 H11Q 109.5 . . ?
H11P C116 H11Q 109.5 . . ?
C106 C116 H11R 109.5 . . ?
H11P C116 H11R 109.5 . . ?
H11Q C116 H11R 109.5 . . ?

_refine_diff_density_max         1.319
_refine_diff_density_min         -1.238
_refine_diff_density_rms         0.101

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1e
_database_code_depnum_ccdc_archive 'CCDC 2504595'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15.50 H22 Cl3 N O2 Ru'
_chemical_formula_weight         461.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.2987(9)
_cell_length_b                   17.9124(6)
_cell_length_c                   8.3465(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.2520(10)
_cell_angle_gamma                90
_cell_volume                     3771.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.6755
_cell_measurement_theta_max      36.6765

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             1864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.262
_shelx_estimated_absorpt_T_min   0.805
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4615
_exptl_absorpt_correction_T_max  0.5680
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1064 (selected reflections only, before parameter refinement)
 R(int) =  0.0550 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25475
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.614
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3563
_reflns_number_gt                3503
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+52.6887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3563
_refine_ls_number_parameters     248
_refine_ls_number_restraints     169
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_restrained_S_all      1.250
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.30561(2) 0.35882(2) 0.34161(5) 0.01354(13) Uani 1 1 d . . . . .
Cl1 Cl 0.37733(5) 0.28894(7) 0.47260(15) 0.0211(3) Uani 1 1 d . . . . .
Cl2 Cl 0.28951(5) 0.40577(7) 0.60375(14) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.3558(2) 0.4414(3) 0.3267(6) 0.0193(11) Uani 1 1 d D . . . .
N1 N 0.3829(7) 0.4945(8) 0.3307(18) 0.015(2) Uani 0.487(4) 1 d D U P A -1
C2 C 0.4145(4) 0.5617(6) 0.3271(12) 0.0170(14) Uani 0.487(4) 1 d D U P A -1
H2A H 0.391043 0.606058 0.322721 0.020 Uiso 0.487(4) 1 calc R U P A -1
H2B H 0.434754 0.561837 0.230118 0.020 Uiso 0.487(4) 1 calc R U P A -1
C3 C 0.4523(4) 0.5649(5) 0.4765(12) 0.0164(14) Uani 0.487(4) 1 d D U P A -1
O1 O 0.4752(3) 0.5119(4) 0.5324(9) 0.0246(18) Uani 0.487(4) 1 d D U P A -1
O2 O 0.4559(3) 0.6338(4) 0.5324(8) 0.0194(16) Uani 0.487(4) 1 d D U P A -1
C4 C 0.4958(5) 0.6470(7) 0.6660(15) 0.033(3) Uani 0.487(4) 1 d D U P A -1
H4A H 0.531066 0.630284 0.636031 0.040 Uiso 0.487(4) 1 calc R U P A -1
H4B H 0.486716 0.618416 0.761613 0.040 Uiso 0.487(4) 1 calc R U P A -1
C5 C 0.4972(6) 0.7272(8) 0.7026(16) 0.042(4) Uani 0.487(4) 1 d D U P A -1
H5A H 0.523716 0.736792 0.791816 0.063 Uiso 0.487(4) 1 calc R U P A -1
H5B H 0.506450 0.755107 0.607673 0.063 Uiso 0.487(4) 1 calc R U P A -1
H5C H 0.462239 0.743276 0.732863 0.063 Uiso 0.487(4) 1 calc R U P A -1
N2 N 0.3871(6) 0.4840(7) 0.2900(17) 0.015(2) Uani 0.513(4) 1 d D U P A -2
C22 C 0.4199(4) 0.5395(5) 0.2250(11) 0.0170(14) Uani 0.513(4) 1 d D U P A -2
H22A H 0.400063 0.563782 0.132524 0.020 Uiso 0.513(4) 1 calc R U P A -2
H22B H 0.451496 0.515119 0.185082 0.020 Uiso 0.513(4) 1 calc R U P A -2
C23 C 0.4377(4) 0.5983(5) 0.3468(11) 0.0164(14) Uani 0.513(4) 1 d D U P A -2
O21 O 0.4218(3) 0.6052(4) 0.4767(9) 0.0252(18) Uani 0.513(4) 1 d D U P A -2
O22 O 0.4718(3) 0.6422(4) 0.2796(8) 0.0168(15) Uani 0.513(4) 1 d D U P A -2
C24 C 0.4872(4) 0.7101(6) 0.3695(13) 0.026(2) Uani 0.513(4) 1 d D U P A -2
H24A H 0.515949 0.698710 0.452825 0.031 Uiso 0.513(4) 1 calc R U P A -2
H24B H 0.456510 0.729868 0.423244 0.031 Uiso 0.513(4) 1 calc R U P A -2
C25 C 0.505(2) 0.7656(6) 0.256(5) 0.038(6) Uani 0.513(4) 1 d D U P A -2
H25A H 0.515805 0.811431 0.313901 0.057 Uiso 0.513(4) 1 calc R U P A -2
H25B H 0.535802 0.745614 0.203688 0.057 Uiso 0.513(4) 1 calc R U P A -2
H25C H 0.476565 0.776665 0.174208 0.057 Uiso 0.513(4) 1 calc R U P A -2
C11 C 0.3019(2) 0.2840(3) 0.1325(6) 0.0197(11) Uani 1 1 d . . . . .
C12 C 0.2677(2) 0.2534(3) 0.2447(6) 0.0191(10) Uani 1 1 d . . . . .
H12 H 0.278026 0.205208 0.298601 0.023 Uiso 1 1 calc R U . . .
C13 C 0.22796(19) 0.2960(3) 0.3073(6) 0.0185(10) Uani 1 1 d . . . . .
H13 H 0.211266 0.277145 0.404470 0.022 Uiso 1 1 calc R U . . .
C14 C 0.2206(2) 0.3733(3) 0.2624(6) 0.0174(10) Uani 1 1 d . . . . .
C15 C 0.25252(19) 0.4029(3) 0.1446(6) 0.0176(10) Uani 1 1 d . . . . .
H15 H 0.251906 0.457783 0.122874 0.021 Uiso 1 1 calc R U . . .
C16 C 0.2924(2) 0.3579(3) 0.0811(6) 0.0205(11) Uani 1 1 d . . . . .
H16 H 0.319142 0.382770 0.016499 0.025 Uiso 1 1 calc R U . . .
C17 C 0.3462(2) 0.2377(3) 0.0731(7) 0.0275(12) Uani 1 1 d . . . . .
H17A H 0.346073 0.188124 0.122921 0.041 Uiso 1 1 calc R U . . .
H17B H 0.341084 0.232516 -0.043908 0.041 Uiso 1 1 calc R U . . .
H17C H 0.380184 0.262238 0.101722 0.041 Uiso 1 1 calc R U . . .
C18 C 0.1781(2) 0.4175(3) 0.3380(6) 0.0211(11) Uani 1 1 d . . . . .
H18 H 0.181521 0.407364 0.456140 0.025 Uiso 1 1 calc R U . . .
C19 C 0.1239(2) 0.3893(3) 0.2719(8) 0.0305(13) Uani 1 1 d . . . . .
H19A H 0.096050 0.417761 0.320381 0.046 Uiso 1 1 calc R U . . .
H19B H 0.120330 0.395903 0.155028 0.046 Uiso 1 1 calc R U . . .
H19C H 0.120384 0.336292 0.297857 0.046 Uiso 1 1 calc R U . . .
C20 C 0.1830(2) 0.5019(3) 0.3140(7) 0.0269(12) Uani 1 1 d . . . . .
H20A H 0.154506 0.527404 0.365576 0.040 Uiso 1 1 calc R U . . .
H20B H 0.217398 0.519044 0.362352 0.040 Uiso 1 1 calc R U . . .
H20C H 0.180340 0.513321 0.198895 0.040 Uiso 1 1 calc R U . . .
C51 C 0.5060(13) 0.929(3) 0.734(4) 0.32(3) Uiso 0.5 1 d D U P B -1
H51A H 0.507898 0.979590 0.687881 0.384 Uiso 0.5 1 calc R U P B -1
H51B H 0.510263 0.890850 0.649408 0.384 Uiso 0.5 1 calc R U P B -1
Cl51 Cl 0.4488(10) 0.9148(18) 0.836(4) 0.403(14) Uiso 0.5 1 d D U P B -1
Cl52 Cl 0.5502(9) 0.9159(16) 0.903(4) 0.377(13) Uiso 0.5 1 d D U P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C1 1.960(5) . ?
Ru1 C16 2.175(5) . ?
Ru1 C15 2.192(5) . ?
Ru1 C11 2.198(5) . ?
Ru1 C14 2.218(5) . ?
Ru1 C12 2.241(5) . ?
Ru1 C13 2.264(5) . ?
Ru1 Cl1 2.4000(13) . ?
Ru1 Cl2 2.4067(12) . ?
C1 N2 1.157(10) . ?
C1 N1 1.172(10) . ?
N1 C2 1.446(12) . ?
C2 C3 1.516(12) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.190(11) . ?
C3 O2 1.320(11) . ?
O2 C4 1.467(12) . ?
C4 C5 1.469(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N2 C22 1.427(11) . ?
C22 C23 1.509(12) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O21 1.191(11) . ?
C23 O22 1.324(10) . ?
O22 C24 1.465(11) . ?
C24 C25 1.47(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C11 C16 1.408(8) . ?
C11 C12 1.430(7) . ?
C11 C17 1.507(7) . ?
C12 C13 1.394(7) . ?
C12 H12 1.0000 . ?
C13 C14 1.443(7) . ?
C13 H13 1.0000 . ?
C14 C15 1.421(7) . ?
C14 C18 1.510(7) . ?
C15 C16 1.423(7) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.527(7) . ?
C18 C20 1.532(8) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C51 Cl51 1.750(17) . ?
C51 Cl52 1.750(17) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ru1 C16 89.7(2) . . ?
C1 Ru1 C15 92.5(2) . . ?
C16 Ru1 C15 38.04(19) . . ?
C1 Ru1 C11 113.6(2) . . ?
C16 Ru1 C11 37.6(2) . . ?
C15 Ru1 C11 68.65(19) . . ?
C1 Ru1 C14 120.8(2) . . ?
C16 Ru1 C14 68.24(18) . . ?
C15 Ru1 C14 37.59(18) . . ?
C11 Ru1 C14 81.43(19) . . ?
C1 Ru1 C12 151.0(2) . . ?
C16 Ru1 C12 66.62(19) . . ?
C15 Ru1 C12 79.07(19) . . ?
C11 Ru1 C12 37.56(19) . . ?
C14 Ru1 C12 67.11(19) . . ?
C1 Ru1 C13 158.1(2) . . ?
C16 Ru1 C13 78.62(18) . . ?
C15 Ru1 C13 66.83(18) . . ?
C11 Ru1 C13 67.08(19) . . ?
C14 Ru1 C13 37.55(18) . . ?
C12 Ru1 C13 36.04(19) . . ?
C1 Ru1 Cl1 87.20(15) . . ?
C16 Ru1 Cl1 120.43(15) . . ?
C15 Ru1 Cl1 158.45(14) . . ?
C11 Ru1 Cl1 91.72(14) . . ?
C14 Ru1 Cl1 151.68(13) . . ?
C12 Ru1 Cl1 90.80(14) . . ?
C13 Ru1 Cl1 114.69(13) . . ?
C1 Ru1 Cl2 87.01(16) . . ?
C16 Ru1 Cl2 152.56(15) . . ?
C15 Ru1 Cl2 114.88(14) . . ?
C11 Ru1 Cl2 159.26(14) . . ?
C14 Ru1 Cl2 90.26(13) . . ?
C12 Ru1 Cl2 121.73(14) . . ?
C13 Ru1 Cl2 94.88(13) . . ?
Cl1 Ru1 Cl2 86.63(4) . . ?
N2 C1 Ru1 166.9(7) . . ?
N1 C1 Ru1 172.7(8) . . ?
C1 N1 C2 176.5(18) . . ?
N1 C2 C3 109.3(10) . . ?
N1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
O1 C3 O2 126.1(9) . . ?
O1 C3 C2 123.5(9) . . ?
O2 C3 C2 110.5(8) . . ?
C3 O2 C4 116.4(8) . . ?
O2 C4 C5 108.6(9) . . ?
O2 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
O2 C4 H4B 110.0 . . ?
C5 C4 H4B 110.0 . . ?
H4A C4 H4B 108.3 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 N2 C22 171.2(17) . . ?
N2 C22 C23 112.5(8) . . ?
N2 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
N2 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
O21 C23 O22 126.8(9) . . ?
O21 C23 C22 125.6(8) . . ?
O22 C23 C22 107.5(7) . . ?
C23 O22 C24 115.6(7) . . ?
O22 C24 C25 108.3(15) . . ?
O22 C24 H24A 110.0 . . ?
C25 C24 H24A 110.0 . . ?
O22 C24 H24B 110.0 . . ?
C25 C24 H24B 110.0 . . ?
H24A C24 H24B 108.4 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 C11 C12 117.5(5) . . ?
C16 C11 C17 122.1(5) . . ?
C12 C11 C17 120.4(5) . . ?
C16 C11 Ru1 70.4(3) . . ?
C12 C11 Ru1 72.9(3) . . ?
C17 C11 Ru1 127.4(4) . . ?
C13 C12 C11 121.7(5) . . ?
C13 C12 Ru1 72.9(3) . . ?
C11 C12 Ru1 69.6(3) . . ?
C13 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
Ru1 C12 H12 118.3 . . ?
C12 C13 C14 120.6(5) . . ?
C12 C13 Ru1 71.1(3) . . ?
C14 C13 Ru1 69.5(3) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
Ru1 C13 H13 118.7 . . ?
C15 C14 C13 118.0(5) . . ?
C15 C14 C18 123.5(5) . . ?
C13 C14 C18 118.5(4) . . ?
C15 C14 Ru1 70.2(3) . . ?
C13 C14 Ru1 72.9(3) . . ?
C18 C14 Ru1 129.8(3) . . ?
C14 C15 C16 120.1(5) . . ?
C14 C15 Ru1 72.2(3) . . ?
C16 C15 Ru1 70.4(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
Ru1 C15 H15 119.4 . . ?
C11 C16 C15 121.9(5) . . ?
C11 C16 Ru1 72.1(3) . . ?
C15 C16 Ru1 71.6(3) . . ?
C11 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
Ru1 C16 H16 118.4 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 C19 108.9(4) . . ?
C14 C18 C20 113.4(4) . . ?
C19 C18 C20 111.0(5) . . ?
C14 C18 H18 107.8 . . ?
C19 C18 H18 107.8 . . ?
C20 C18 H18 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Cl51 C51 Cl52 95.2(13) . . ?
Cl51 C51 H51A 112.7 . . ?
Cl52 C51 H51A 112.7 . . ?
Cl51 C51 H51B 112.7 . . ?
Cl52 C51 H51B 112.7 . . ?
H51A C51 H51B 110.2 . . ?

_refine_diff_density_max         1.221
_refine_diff_density_min         -0.984
_refine_diff_density_rms         0.123

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2c
_database_code_depnum_ccdc_archive 'CCDC 2504597'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H29 Cl2 N O Ru'
_chemical_formula_weight         483.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3074(4)
_cell_length_b                   12.8439(7)
_cell_length_c                   22.1781(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2081.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9588
_cell_measurement_theta_min      2.4265
_cell_measurement_theta_max      36.546

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.020
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4581
_exptl_absorpt_correction_T_max  0.5680
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1244 (selected reflections only, before parameter refinement)
 R(int) =  0.0580 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32825
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.832
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5026
_reflns_number_gt                5003
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+1.5963P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2128 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5026
_refine_ls_number_parameters     248
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0530
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.61654(3) 0.73565(2) 0.34944(2) 0.01174(6) Uani 1 1 d . . . . .
Cl1 Cl 0.35787(10) 0.62872(6) 0.37674(3) 0.01917(14) Uani 1 1 d . . . . .
Cl2 Cl 0.40700(10) 0.88110(5) 0.34355(3) 0.01913(14) Uani 1 1 d . . . . .
N1 N 0.5318(4) 0.6854(2) 0.21513(12) 0.0178(5) Uani 1 1 d . . . . .
C1 C 0.5567(4) 0.7050(2) 0.26511(13) 0.0141(5) Uani 1 1 d . . . . .
C2 C 0.4976(4) 0.6630(2) 0.15171(14) 0.0158(5) Uani 1 1 d . . . . .
H2 H 0.487395 0.585796 0.146810 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3166(4) 0.7116(3) 0.13328(14) 0.0217(7) Uani 1 1 d . . . . .
H3A H 0.218290 0.683808 0.158661 0.033 Uiso 1 1 calc R U . . .
H3B H 0.291252 0.695181 0.090944 0.033 Uiso 1 1 calc R U . . .
H3C H 0.323350 0.787347 0.138336 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6569(4) 0.7007(2) 0.11369(13) 0.0168(6) Uani 1 1 d . . . . .
C5 C 0.6937(5) 0.8067(3) 0.10836(16) 0.0245(7) Uani 1 1 d . . . . .
H5 H 0.624806 0.855892 0.130901 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8322(5) 0.8402(3) 0.06975(17) 0.0301(8) Uani 1 1 d . . . . .
H6 H 0.855747 0.912548 0.065505 0.036 Uiso 1 1 calc R U . . .
C7 C 0.9346(4) 0.7701(4) 0.03794(15) 0.0311(8) Uani 1 1 d . . . . .
H7 H 1.030030 0.793788 0.012263 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8991(5) 0.6642(3) 0.04317(15) 0.0273(7) Uani 1 1 d . . . . .
H8 H 0.969187 0.615559 0.020648 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7606(4) 0.6294(3) 0.08150(14) 0.0213(6) Uani 1 1 d . . . . .
H9 H 0.737414 0.556943 0.085535 0.026 Uiso 1 1 calc R U . . .
C11 C 0.9068(4) 0.7578(3) 0.32479(13) 0.0204(6) Uani 1 1 d . . . . .
C12 C 0.8796(4) 0.6518(2) 0.34377(14) 0.0197(6) Uani 1 1 d . . . . .
C13 C 0.7994(4) 0.6312(2) 0.40060(14) 0.0176(6) Uani 1 1 d . . . . .
C14 C 0.7528(4) 0.7164(2) 0.44077(13) 0.0160(6) Uani 1 1 d . . . . .
C15 C 0.7769(4) 0.8201(2) 0.42168(14) 0.0161(6) Uani 1 1 d . . . . .
C16 C 0.8494(4) 0.8407(2) 0.36225(13) 0.0170(6) Uani 1 1 d . . . . .
C21 C 0.9937(5) 0.7798(4) 0.26417(16) 0.0351(9) Uani 1 1 d . . . . .
H21A H 0.981508 0.854015 0.254713 0.053 Uiso 1 1 calc R U . . .
H21B H 0.932259 0.738538 0.233007 0.053 Uiso 1 1 calc R U . . .
H21C H 1.123661 0.761097 0.265549 0.053 Uiso 1 1 calc R U . . .
C22 C 0.9361(5) 0.5640(3) 0.30218(18) 0.0325(9) Uani 1 1 d . . . . .
H22A H 1.062981 0.544191 0.310738 0.049 Uiso 1 1 calc R U . . .
H22B H 0.926035 0.587028 0.260187 0.049 Uiso 1 1 calc R U . . .
H22C H 0.855827 0.503915 0.308715 0.049 Uiso 1 1 calc R U . . .
C23 C 0.7642(5) 0.5219(3) 0.42170(18) 0.0277(7) Uani 1 1 d . . . . .
H23A H 0.804046 0.472627 0.390611 0.042 Uiso 1 1 calc R U . . .
H23B H 0.633053 0.512693 0.429266 0.042 Uiso 1 1 calc R U . . .
H23C H 0.832512 0.509003 0.458985 0.042 Uiso 1 1 calc R U . . .
C24 C 0.6759(5) 0.6900(3) 0.50206(14) 0.0244(7) Uani 1 1 d . . . . .
H24A H 0.740401 0.629358 0.518438 0.037 Uiso 1 1 calc R U . . .
H24B H 0.545275 0.673999 0.498313 0.037 Uiso 1 1 calc R U . . .
H24C H 0.692147 0.749461 0.529218 0.037 Uiso 1 1 calc DR U . . .
C25 C 0.7162(5) 0.9104(3) 0.46090(15) 0.0250(7) Uani 1 1 d . . . . .
H25A H 0.638400 0.884389 0.493594 0.038 Uiso 1 1 calc DR U . . .
H25B H 0.646993 0.960258 0.436425 0.038 Uiso 1 1 calc DR U . . .
H25C H 0.823904 0.944910 0.478020 0.038 Uiso 1 1 calc R U . . .
C26 C 0.8748(5) 0.9515(2) 0.34123(16) 0.0285(7) Uani 1 1 d . . . . .
H26A H 1.005762 0.966911 0.337951 0.043 Uiso 1 1 calc R U . . .
H26B H 0.818423 0.999108 0.370340 0.043 Uiso 1 1 calc DR U . . .
H26C H 0.816663 0.960439 0.301747 0.043 Uiso 1 1 calc R U . . .
O1 O 0.4734(9) 0.9410(3) 0.20538(19) 0.0804(16) Uani 1 1 d D . . . .
H12 H 0.542(10) 1.004(4) 0.200(4) 0.121 Uiso 1 1 d D U . . .
H11 H 0.457(12) 0.937(6) 0.2477(13) 0.121 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C1 1.961(3) . ?
Ru1 C16 2.190(3) . ?
Ru1 C12 2.207(3) . ?
Ru1 C13 2.207(3) . ?
Ru1 C11 2.209(3) . ?
Ru1 C15 2.262(3) . ?
Ru1 C14 2.271(3) . ?
Ru1 Cl1 2.4136(8) . ?
Ru1 Cl2 2.4190(7) . ?
N1 C1 1.151(4) . ?
N1 C2 1.457(4) . ?
C2 C4 1.517(4) . ?
C2 C3 1.519(4) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C9 1.387(5) . ?
C4 C5 1.393(5) . ?
C5 C6 1.394(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.367(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C16 1.414(4) . ?
C11 C12 1.439(4) . ?
C11 C21 1.514(4) . ?
C12 C13 1.415(4) . ?
C12 C22 1.515(4) . ?
C13 C14 1.451(4) . ?
C13 C23 1.502(4) . ?
C14 C15 1.408(4) . ?
C14 C24 1.509(4) . ?
C15 C16 1.445(4) . ?
C15 C25 1.516(4) . ?
C16 C26 1.509(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O1 H12 0.96(3) . ?
O1 H11 0.95(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ru1 C16 114.88(11) . . ?
C1 Ru1 C12 92.40(12) . . ?
C16 Ru1 C12 68.35(11) . . ?
C1 Ru1 C13 120.21(12) . . ?
C16 Ru1 C13 80.64(11) . . ?
C12 Ru1 C13 37.40(11) . . ?
C1 Ru1 C11 90.23(11) . . ?
C16 Ru1 C11 37.49(11) . . ?
C12 Ru1 C11 38.03(12) . . ?
C13 Ru1 C11 67.94(12) . . ?
C1 Ru1 C15 152.57(12) . . ?
C16 Ru1 C15 37.84(11) . . ?
C12 Ru1 C15 79.80(11) . . ?
C13 Ru1 C15 67.27(11) . . ?
C11 Ru1 C15 67.42(11) . . ?
C1 Ru1 C14 157.95(11) . . ?
C16 Ru1 C14 67.09(11) . . ?
C12 Ru1 C14 67.40(11) . . ?
C13 Ru1 C14 37.79(11) . . ?
C11 Ru1 C14 79.26(11) . . ?
C15 Ru1 C14 36.20(11) . . ?
C1 Ru1 Cl1 87.15(9) . . ?
C16 Ru1 Cl1 157.89(8) . . ?
C12 Ru1 Cl1 114.76(9) . . ?
C13 Ru1 Cl1 89.96(9) . . ?
C11 Ru1 Cl1 152.56(9) . . ?
C15 Ru1 Cl1 120.05(9) . . ?
C14 Ru1 Cl1 93.30(8) . . ?
C1 Ru1 Cl2 87.85(8) . . ?
C16 Ru1 Cl2 91.32(8) . . ?
C12 Ru1 Cl2 157.67(9) . . ?
C13 Ru1 Cl2 151.67(8) . . ?
C11 Ru1 Cl2 119.66(9) . . ?
C15 Ru1 Cl2 89.77(8) . . ?
C14 Ru1 Cl2 114.20(8) . . ?
Cl1 Ru1 Cl2 87.55(3) . . ?
C1 N1 C2 178.6(3) . . ?
N1 C1 Ru1 176.1(3) . . ?
N1 C2 C4 110.0(2) . . ?
N1 C2 C3 109.1(2) . . ?
C4 C2 C3 112.8(2) . . ?
N1 C2 H2 108.3 . . ?
C4 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 119.8(3) . . ?
C9 C4 C2 119.6(3) . . ?
C5 C4 C2 120.5(3) . . ?
C4 C5 C6 119.6(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C4 C9 C8 119.9(3) . . ?
C4 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C16 C11 C12 120.0(3) . . ?
C16 C11 C21 120.4(3) . . ?
C12 C11 C21 119.6(3) . . ?
C16 C11 Ru1 70.56(16) . . ?
C12 C11 Ru1 70.91(17) . . ?
C21 C11 Ru1 130.3(2) . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 C22 121.0(3) . . ?
C11 C12 C22 119.3(3) . . ?
C13 C12 Ru1 71.33(17) . . ?
C11 C12 Ru1 71.06(16) . . ?
C22 C12 Ru1 129.5(2) . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 C23 121.6(3) . . ?
C14 C13 C23 118.2(3) . . ?
C12 C13 Ru1 71.27(17) . . ?
C14 C13 Ru1 73.46(17) . . ?
C23 C13 Ru1 128.6(2) . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 C24 122.0(3) . . ?
C13 C14 C24 118.1(3) . . ?
C15 C14 Ru1 71.56(17) . . ?
C13 C14 Ru1 68.75(17) . . ?
C24 C14 Ru1 131.7(2) . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 C25 121.0(3) . . ?
C16 C15 C25 119.3(3) . . ?
C14 C15 Ru1 72.24(17) . . ?
C16 C15 Ru1 68.40(16) . . ?
C25 C15 Ru1 128.4(2) . . ?
C11 C16 C15 120.4(3) . . ?
C11 C16 C26 119.5(3) . . ?
C15 C16 C26 120.0(3) . . ?
C11 C16 Ru1 71.95(17) . . ?
C15 C16 Ru1 73.75(17) . . ?
C26 C16 Ru1 129.5(2) . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C14 C24 H24A 109.5 . . ?
C14 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C14 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C25 H25A 109.5 . . ?
C15 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C15 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 C26 H26A 109.5 . . ?
C16 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C16 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H12 O1 H11 103(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 Cl2 1.00 2.75 3.688(3) 156.8 3_645 yes
O1 H12 Cl1 0.96(3) 2.45(6) 3.263(4) 142(7) 3_655 yes
O1 H11 Cl2 0.95(3) 2.27(3) 3.197(4) 164(7) . yes

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.066

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1bI
_database_code_depnum_ccdc_archive 'CCDC 2504598'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H25 I2 N Ru'
_chemical_formula_weight         598.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7509(6)
_cell_length_b                   16.0618(10)
_cell_length_c                   12.8319(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.133(2)
_cell_angle_gamma                90
_cell_volume                     1984.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9797
_cell_measurement_theta_min      2.4665
_cell_measurement_theta_max      35.703

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.003
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    3.897
_shelx_estimated_absorpt_T_min   0.495
_shelx_estimated_absorpt_T_max   0.674
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2420
_exptl_absorpt_correction_T_max  0.3867
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1712 (selected reflections only, before parameter refinement)
 R(int) =  0.0670 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTONII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27260
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4310
_reflns_number_gt                4113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0114P)²+6.7612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4310
_refine_ls_number_parameters     193
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_restrained_S_all      1.303
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.57428(3) 0.61710(2) 0.67722(2) 0.00881(7) Uani 1 1 d . . . . .
I1 I 0.82261(3) 0.57017(2) 0.62595(2) 0.01368(7) Uani 1 1 d . . . . .
I2 I 0.51968(3) 0.70271(2) 0.49300(2) 0.01562(7) Uani 1 1 d . . . . .
N1 N 0.7353(4) 0.7729(2) 0.7731(3) 0.0167(7) Uani 1 1 d . . . . .
C1 C 0.6757(4) 0.7168(3) 0.7345(3) 0.0142(8) Uani 1 1 d . . . . .
C2 C 0.8224(4) 0.8372(3) 0.8291(3) 0.0168(8) Uani 1 1 d . U . . .
H2 H 0.765926 0.869066 0.874094 0.020 Uiso 1 1 calc R U . . .
C3 C 0.8706(5) 0.8967(3) 0.7506(4) 0.0228(9) Uani 1 1 d . . . . .
H3A H 0.915292 0.945690 0.788599 0.027 Uiso 1 1 calc R U . . .
H3B H 0.789189 0.916490 0.700603 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9737(5) 0.8545(3) 0.6889(4) 0.0260(10) Uani 1 1 d . . . . .
H4A H 0.925806 0.809607 0.644433 0.031 Uiso 1 1 calc R U . . .
H4B H 1.007923 0.895774 0.641823 0.031 Uiso 1 1 calc R U . . .
C5 C 1.0965(5) 0.8180(3) 0.7633(4) 0.0224(9) Uani 1 1 d . . . . .
H5A H 1.159940 0.789753 0.721577 0.027 Uiso 1 1 calc R U . . .
H5B H 1.148759 0.863422 0.804022 0.027 Uiso 1 1 calc R U . . .
C6 C 1.0473(5) 0.7560(3) 0.8391(4) 0.0216(9) Uani 1 1 d . . . . .
H6A H 1.128053 0.735185 0.888924 0.026 Uiso 1 1 calc R U . . .
H6B H 1.002966 0.707832 0.798893 0.026 Uiso 1 1 calc R U . . .
C7 C 0.9437(5) 0.7964(3) 0.9008(3) 0.0241(10) Uani 1 1 d . . . . .
H7A H 0.992334 0.839110 0.948726 0.029 Uiso 1 1 calc R U . . .
H7B H 0.907293 0.753662 0.944720 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3464(4) 0.5896(3) 0.6668(3) 0.0172(8) Uani 1 1 d . . . . .
C12 C 0.3967(4) 0.6272(3) 0.7646(3) 0.0154(8) Uani 1 1 d . . . . .
H12 H 0.361888 0.683619 0.780512 0.018 Uiso 1 1 calc R U . . .
C13 C 0.5149(4) 0.5940(3) 0.8305(3) 0.0142(8) Uani 1 1 d . . . . .
H13 H 0.559713 0.627714 0.892181 0.017 Uiso 1 1 calc R U . . .
C14 C 0.5838(4) 0.5218(2) 0.8024(3) 0.0136(8) Uani 1 1 d . . . . .
C15 C 0.5281(4) 0.4833(2) 0.7035(3) 0.0132(7) Uani 1 1 d . . . . .
H15 H 0.585319 0.440090 0.674337 0.016 Uiso 1 1 calc R U . . .
C16 C 0.4137(4) 0.5161(3) 0.6374(3) 0.0156(8) Uani 1 1 d . U . . .
H16 H 0.392059 0.495733 0.562933 0.019 Uiso 1 1 calc R U . . .
C17 C 0.2227(4) 0.6243(3) 0.5954(4) 0.0242(10) Uani 1 1 d . . . . .
H17A H 0.137369 0.604584 0.618563 0.036 Uiso 1 1 calc R U . . .
H17B H 0.224455 0.605809 0.522848 0.036 Uiso 1 1 calc R U . . .
H17C H 0.225591 0.685306 0.598162 0.036 Uiso 1 1 calc R U . . .
C18 C 0.7084(5) 0.4836(3) 0.8708(3) 0.0204(9) Uani 1 1 d . . . . .
H18 H 0.771135 0.461918 0.822550 0.024 Uiso 1 1 calc R U . . .
C19 C 0.7912(6) 0.5454(4) 0.9444(5) 0.0455(16) Uani 1 1 d . . . . .
H19A H 0.820263 0.591757 0.903299 0.068 Uiso 1 1 calc R U . . .
H19B H 0.873522 0.517808 0.983136 0.068 Uiso 1 1 calc R U . . .
H19C H 0.733628 0.566654 0.994544 0.068 Uiso 1 1 calc R U . . .
C20 C 0.6596(7) 0.4091(4) 0.9287(6) 0.0547(19) Uani 1 1 d . . . . .
H20A H 0.599458 0.428334 0.978163 0.082 Uiso 1 1 calc R U . . .
H20B H 0.740357 0.380231 0.967707 0.082 Uiso 1 1 calc R U . . .
H20C H 0.607698 0.370854 0.877476 0.082 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C1 1.962(4) . ?
Ru1 C13 2.168(4) . ?
Ru1 C14 2.210(4) . ?
Ru1 C12 2.213(4) . ?
Ru1 C15 2.232(4) . ?
Ru1 C11 2.248(4) . ?
Ru1 C16 2.256(4) . ?
Ru1 I2 2.7134(4) . ?
Ru1 I1 2.7148(4) . ?
N1 C1 1.142(5) . ?
N1 C2 1.453(5) . ?
C2 C3 1.517(6) . ?
C2 C7 1.525(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.532(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.526(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.522(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.524(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 C12 1.409(6) . ?
C11 C16 1.431(6) . ?
C11 C17 1.501(6) . ?
C12 C13 1.420(6) . ?
C12 H12 1.0000 . ?
C13 C14 1.415(6) . ?
C13 H13 1.0000 . ?
C14 C15 1.438(6) . ?
C14 C18 1.512(6) . ?
C15 C16 1.393(6) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.512(7) . ?
C18 C20 1.524(7) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ru1 C13 89.50(16) . . ?
C1 Ru1 C14 109.42(16) . . ?
C13 Ru1 C14 37.70(15) . . ?
C1 Ru1 C12 97.99(16) . . ?
C13 Ru1 C12 37.81(15) . . ?
C14 Ru1 C12 68.18(15) . . ?
C1 Ru1 C15 146.16(16) . . ?
C13 Ru1 C15 67.00(15) . . ?
C14 Ru1 C15 37.78(14) . . ?
C12 Ru1 C15 78.54(15) . . ?
C1 Ru1 C11 128.11(16) . . ?
C13 Ru1 C11 67.49(15) . . ?
C14 Ru1 C11 80.47(15) . . ?
C12 Ru1 C11 36.82(15) . . ?
C15 Ru1 C11 66.37(15) . . ?
C1 Ru1 C16 164.15(16) . . ?
C13 Ru1 C16 78.89(15) . . ?
C14 Ru1 C16 67.31(15) . . ?
C12 Ru1 C16 66.24(15) . . ?
C15 Ru1 C16 36.17(15) . . ?
C11 Ru1 C16 37.04(15) . . ?
C1 Ru1 I2 86.00(12) . . ?
C13 Ru1 I2 146.41(11) . . ?
C14 Ru1 I2 164.57(11) . . ?
C12 Ru1 I2 110.07(11) . . ?
C15 Ru1 I2 127.10(10) . . ?
C11 Ru1 I2 89.54(11) . . ?
C16 Ru1 I2 97.69(11) . . ?
C1 Ru1 I1 84.32(12) . . ?
C13 Ru1 I1 123.31(11) . . ?
C14 Ru1 I1 92.74(10) . . ?
C12 Ru1 I1 160.52(11) . . ?
C15 Ru1 I1 88.76(10) . . ?
C11 Ru1 I1 147.36(11) . . ?
C16 Ru1 I1 111.03(11) . . ?
I2 Ru1 I1 89.357(12) . . ?
C1 N1 C2 173.2(4) . . ?
N1 C1 Ru1 176.2(4) . . ?
N1 C2 C3 109.7(3) . . ?
N1 C2 C7 109.3(4) . . ?
C3 C2 C7 112.2(4) . . ?
N1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C7 C2 H2 108.5 . . ?
C2 C3 C4 111.2(4) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 111.2(4) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 110.8(4) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 110.8(4) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C2 112.6(4) . . ?
C6 C7 H7A 109.1 . . ?
C2 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C2 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C12 C11 C16 118.6(4) . . ?
C12 C11 C17 121.1(4) . . ?
C16 C11 C17 120.2(4) . . ?
C12 C11 Ru1 70.2(2) . . ?
C16 C11 Ru1 71.8(2) . . ?
C17 C11 Ru1 130.9(3) . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 Ru1 73.0(2) . . ?
C13 C12 Ru1 69.4(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
Ru1 C12 H12 119.2 . . ?
C14 C13 C12 121.9(4) . . ?
C14 C13 Ru1 72.7(2) . . ?
C12 C13 Ru1 72.8(2) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
Ru1 C13 H13 118.7 . . ?
C13 C14 C15 116.7(4) . . ?
C13 C14 C18 123.7(4) . . ?
C15 C14 C18 119.6(4) . . ?
C13 C14 Ru1 69.6(2) . . ?
C15 C14 Ru1 71.9(2) . . ?
C18 C14 Ru1 129.8(3) . . ?
C16 C15 C14 121.9(4) . . ?
C16 C15 Ru1 72.9(2) . . ?
C14 C15 Ru1 70.3(2) . . ?
C16 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
Ru1 C15 H15 118.3 . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 Ru1 71.0(2) . . ?
C11 C16 Ru1 71.2(2) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
Ru1 C16 H16 119.1 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 C19 113.4(4) . . ?
C14 C18 C20 108.5(4) . . ?
C19 C18 C20 112.8(5) . . ?
C14 C18 H18 107.3 . . ?
C19 C18 H18 107.3 . . ?
C20 C18 H18 107.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         1.185
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.142

